Factually! with Adam Conover - Why Are Men So Afraid of Fashion with Derek Guy

Episode Date: October 9, 2024

Fashion is one of the most overlooked ways we express ourselves. What we wear tells stories about our time, place, class, gender, and so much more. So, it’s a real shame that fashion—especially men’s fashion—often gets brushed off as frivolous or dismissed (wrongfully) as “too feminine.” This week, Adam chats with menswear writer and Twitter icon Derek Guy about the fascinating history of men’s fashion and where we stand in today’s style landscape.SUPPORT THE SHOW ON PATREON: https://www.patreon.com/adamconoverSEE ADAM ON TOUR: https://www.adamconover.net/tourdates/SUBSCRIBE to and RATE Factually! on:» Apple Podcasts: https://podcasts.apple.com/us/podcast/factually-with-adam-conover/id1463460577» Spotify: https://open.spotify.com/show/0fK8WJw4ffMc2NWydBlDyJAbout Headgum: Headgum is an LA & NY-based podcast network creating premium podcasts with the funniest, most engaging voices in comedy to achieve one goal: Making our audience and ourselves laugh. Listen to our shows at https://www.headgum.com.» SUBSCRIBE to Headgum: https://www.youtube.com/c/HeadGum?sub_confirmation=1» FOLLOW us on Twitter: http://twitter.com/headgum» FOLLOW us on Instagram: https://instagram.com/headgum/» FOLLOW us on TikTok: https://www.tiktok.com/@headgum» Advertise on Factually! via Gumball.fmSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This is a HeadGum Podcast. You know, we're under a month from Election Day, and if you're anything like me, you've been thinking, why does it feel like American democracy is unraveling before my eyes? Well, the answer is that it's the fault of our electoral system and its winner-take-all ideology. But is this centuries-old system really the best we have in 2024? Well, spoiler, no, it isn't. And to learn more, I highly recommend

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I don't know the way. I don't know what to think. I don't know what to say. Yeah, but that's all right. That's OK. I don't know anything. Hello and welcome to Factually. I don't know anything. Hello and welcome to Factually. I'm Adam Conover. Thanks for joining me on the show again.

You know, I'm a guy who likes to dress well. Even when I dressed badly when I was younger, and I definitely did dress badly, I still cared about my clothes and I cared about giving the impression of myself that I wanted to, to the world. But not everyone around me has over the course of my life. I remember a couple years ago,

I was having a conversation with a male friend who claimed that he did not care about clothes at all. He didn't care about what other people wore and he didn't care about what he wore. Now, if he really didn't care about clothes, he could have worn literally anything, right? He could have worn a bed sheet toga, he could have worn an old suit from the thrift store.

He could have worn a loincloth that made out of McDonald's napkins. But he didn't do that. Instead, he wore Nike slides, gym shorts, and a T-shirt every single day. He didn't not care about clothes. He instead had learned to dress in a style that communicated how much he did not care about clothes.

He was speaking in the very visual language he claimed to be ignorant of, not just speaking in it, but commenting on it. The point is that clothing and fashion is as complex and meaningful as any other aspect of culture and is in fact a means of communication. But in our society, there's an undercurrent of suspicion when it comes to fashion, especially for men who care about fashion.

Paying attention to clothing is deemed frivolous, or worse, feminine. But when we treat it that way, we miss out on an entire world of human expression, one that we all participate in, whether or not we know it. So on the show today, we have one of my very favorite people on the internet and one of the best commentators working today on clothing and fashion and what it means to society as a form of social language. But before we get into that, I want to remind you that if you want to support this show

and all the conversations we bring you every single week, you can do so on Patreon. Head to patreon.com slash Adam Conover. Just five bucks a month gets you every episode of the show ad free, we'd love every single week. You can do so on Patreon. Head to patreon.com slash Adam Conover. Just five bucks a month gets you every episode of this show ad free. We'd love to have you. And just to remind you, my new stand-up special Unmedicated is out now on Dropout. Head to dropout.tv to subscribe and stream it.

And if you want to come see me do stand-up comedy live, coming up soon, I'm headed to Portland, Oregon, Seattle, Washington, Denver, Colorado, Austin, Texas, Patavia, Illinois, San Francisco, California, Seattle, Washington, Denver, Colorado, Austin, Texas, Petavia, Illinois, San Francisco, California, Toronto, Canada, Chicago, Illinois, Boston, Massachusetts, and Providence, Rhode Island. Head to adamconover.net for tickets and tour dates. And now let's get to this week's episode. My guest today is Derek Guy.

He's a menswear writer and one of the best posters on the internet, period. His tweets are not only incredibly thoughtful and eye-opening with a seemingly encyclopedic knowledge of both the technical aspects of men's fashion and its history, but they are funny and perfectly poised. I'm so excited to have him on the show. Now, I wanna let you know,

Derek chooses not to share his appearance on the internet, which is something that we respect. So if you're watching via YouTube, you will see him via a little avatar that we have put up, but he has also agreed to share some images from his voluminous archive to help illustrate our discussion that you'll have plenty to look at during the podcast.

Without further ado, please welcome Derek Guy. Derek, thank you so much for being on the show. Thanks so much for having me. I have been reading your work on Put This On and on many of the other publications you write for many, many years. Although in the last couple of years, you have found yourself in the position

of going mega viral on Twitter for your menswear takes. How did that happen and how did you get into writing about this, reading about it, and learning about it in the first place? Well, I got interested in clothing, you know, just as a young person. I mean, when you're young, you're interested in, you know, kind of music and whatnot.

And I got my interest in clothing through music. And then in the early 2000s, fell into menswear forums and blogs, and kind of was part of a kind of clothing hobbyist community for a while. Started a blog in 2011, I think, and then joined Twitter shortly after. And then all of a sudden, I think it was maybe in 2022 when my account started going viral on Twitter. And it specifically went viral in this way where it was showing up on people's For You pages. Twitter had like recently,

I think this is around the time of the Elon Musk takeover, had really doubled down on algorithmic timeline and certain things just sort of took wing. And you specifically doing threads about often public figures and their clothes and what we can learn about via their clothes and by the mistakes that they make, really started to catch with people to the extent that people were going,

why is this menswear guy on my timeline all the time? What do you credit them going that viral to? You know, like, is there anything about it that captured the public imagination, do you think? I honestly have no idea why anyone follows me, why anyone likes my cat. I'm just genuinely baffling to me In I think it was like October or November of 2022 Dave Portnoy of Barstool sports started a watch company called Brick Watches and I

I said that they were ripoff He was trying to sell these two these watches for two thousand three hundred dollars And I said inside one of them is a $40 quartz movement. And this is a ripoff and I wouldn't even do this to my enemies. I certainly would not sell this to people that support me. And then he did a video about it, responding to it, where he mentioned me.

And I thought that was so funny because that was like, I'm an absolute nobody and this is a huge public figure that noticed me, I just thought it was hilarious. And then somebody replied to that and said, well, how is what Dave's doing different than what Ralph Lauren does when they buy cashmere sweaters and sell them for $500. So I did this whole thread on what makes a good

cashmere sweater and why buying cheap cashmere is bad. And that went viral. And a bunch of newspapers called me for quotes. And that was like one of the first times I kind of, you know, I was on Twitter from like 2011 to, I mean, until today. And for the majority of that period, I was tweeting basically like in-group jokes to other menswear nerds. And that cashmere thread was the first time I kind of like quote unquote broke character

and did something that I was trying to be more informative instead of just making jokes about you know like niche brands. And a lot of people liked it. So then I started to do more of them and that was in the end of 2022. And then in the beginning of 2023, I started noticing a lot of people. I mean, after the Barstool sports thing, a lot of people tweeted me like, who cares? You're stupid. You're a moron. Like this is dumb.

But in 2000, start of 2023, I would get those replies seemingly from people who had just like found me without a retweet. And I would be like, why would you go to my account and then just say this? Like, that doesn't make any sense. And then I realized I was getting picked up by the algorithm. And then, yeah, since people found those informative threads useful,

I just kept on doing more of them. I did one on how much it costs to make a dress shirt in the United States, how to dress if you're a larger guy, what goes into how to find your right shoe size, basic things like that. And yeah, people find it useful, yes. And you've got in there a nice sprinkling

of making fun of public figures who are dressing poorly. You are on Daniel Craig's ass, his finely muscled ass all the time. You've, I think, gone after folks like Matt Gaetz on occasion, people like that. But what I, and that gives, you know, a certain amount of visceral appeal to the tweet threads. But what I love about what you do,

and by the way, for folks listening, it's not just Twitter, your byline is at tons of, tons of different publications. You did a wonderful piece where you talked about all the clothing choices made by speakers at the DNC, for example, which I thought was really interesting. What I love about that is, about your writing, is you don't just talk about, hey, here's what looks good, here's what doesn't look good,

or here's a tip, you also contextualize it within the history and the social language of clothing and where these things come from and what they mean. And so I'd love to get into that a little bit. Is that what, in in your view makes it interesting and important to talk about clothes? Is clothing as a social language? That is just my personal view of clothes.

So my view of clothes is that it's a form of social language and that's always how I've understood clothes. And I think if you grew up in the eighties and nineties, that's very obvious to you because you probably went to school at a time where there were jocks and there were goths and skaters and punks and all of these subcultural groups. And probably-

And I'm just picturing, I'm just picturing the clothes that they're wearing. When you say those groups, I'm literally picturing outfits. Right, so to me, it's like, when you are in those groups, you are probably not interested in fashion, but you probably dress a certain way according to your group.

And you dress in a way to identify yourself as part of the group, but also to show that you're an individual within that group. And I think when you think of clothes in that type of social language, that's to me how I think fashion works. But also I do think it makes it more interesting. I was I think it was sometime in 2023, a Washington Post editor called me and asked if I was interested in writing for them. And I said, and this is not to slander anyone's work.

You know, I realize everyone is approaching this from their own perspective and voice, and I think that's totally fine. But I was just telling you, honestly, I don't read that many fashion articles because a lot of fashion articles feel disconnected from my life. They're about like how a creative director

got appointed at this luxury firm, or you know, like the trending it bag, and like what five, you know, like trendy New Yorkers are wearing. And it just feels very disconnected from my life. And I would be much more interested in hearing about like the rise and decline of pajamas, you know, like socially, why don't we stop wearing pajamas?

Or I'd rather read about a group of Japanese hikers in the 1970s who spun out craze for a certain kind of like hiking style or something. To me, those stories are much more interesting and they are more human. I think of fashion as an interesting topic because any time that you tell any story that involves humans,

there is a component of fashion in there because humans wear clothing. So anytime you talk about war or trade or gender, sexuality, anything that deals with humans, there's probably some story in there about fashion. That's really fascinating, but a lot of times, the story of fashion is treated as trivial. Oh, fashion changes, so there's no reason

why one would wear one thing at one time or another thing at another time. Oh, in Mad Men, they dressed like this in the 60s. Today we dress like that. In, you know, da-da-da-da-da. You know, lapels get wider, lapels get narrower. Who gives a shit, right? It's just sort of waves washing up on the beach

of human behavior. That I think is a very common view of fashion. Why is it incorrect? Well, I don't think anyone has to pay any particularly strong interest in fashion. I think of it as just a hobby, but I do think that the people who pretend that they don't care about fashion at all are lying,

because for example, if you gave a man the choice between a free pair of pink jeans and a pair of blue jeans that he had to pay $50 for, many will still shell out the $50 because what they think the colors represent. So even people who pretend that they don't care about clothing have certain preferences for how things look because they are cued into what clothes mean. If you arrived at a funeral and somebody came with a, you know, like a birthday party hat,

you'd assume something about what they thought of the person in the casket, right? So, I mean, these are all extremes, but I think it's also true, like, when you go to work in a professional setting, you kind of know what clothes to wear. So I think people who pretend that they don't care about clothing do think about it to some degree. But it is true that historically in Western society, clothing has been considered frivolous.

When you read Greek philosophers, I mean, the famous story of the emperor has no clothes, this is about a very vain man. Everyone laughs at him because he's obsessed with something that doesn't matter. So historically, Western society has always thought fashion was frivolous and these are fleeting trends. And as such, since fashion was considered frivolous, it was historically considered the purview of women who were excluded from positions of power and influence, academia, science, business, so on and so forth. So throughout history, fashion has been coded as both historically frivolous and feminine, which puts up a certain kind of barrier to many people enjoying it.

Now it's only really within the last few decades where you see academia taking fashion, clothing as a more serious form of study. And again, I think to me, it's undeniable that clothing is important because one of the biggest political fights today is about clothing. It's about whether or not men can, you know, how gender is expressed through different clothes, whether, you know, if you know, if you're assigned male or female at birth, are you expected to wear sundresses and nobody really wears suits anymore,

but you know, whatever, like flannel shirts and jeans or whatever. So to me, this is like, it's very much at the forefront of politics and we do know that clothing is important because we have huge political fights over it. Right, because gender has become a really important political issue, for better or worse,

and our ideas of clothing are sort of inextricably tied up with our ideas about gender. And one of the things that's really interesting is you, a lot of times when you're critiquing, again, the clothes worn by male public figures, you're talking about they are trying to self-consciously dress in a way that they perceive as masculine, but which in your view sort of undermines the fit or,

you know, look, at the very least looks bad, but also is sort of like a historic in how it's connected to gender. I find that sort of analysis like really interesting. And it just goes to show how much depth there is when you start talking about clothing, like what each article of clothing means and what its history is and even just the,

I don't know, the history of the suit itself. You know, I've talked a lot on this show about how important it is to support quality journalism, which is why I am so excited to share that this episode is sponsored by the Washington Post. If you're a factually listener, I'm willing to bet that you're someone who likes to stay informed and engaged, and so am I.

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for 30% off your first order, plus a free $60 gift. That's T-H-R-I-V-E market.com slash factually, thrivemarket.com slash factually. There's so many things I want to talk to you about, I don't even know where to start. You said there, nobody wears suits anymore. I'd love to talk for a little bit about, like just to zoom in on one article of clothing,

the suit itself, like where does it come from and why do we, you know, why do people begin to wear them? And why have we largely stopped wearing them today to the point where even politicians who, you know, previously had to wear them are now, you know, taking them off as a lot more often. Well, the popular narrative of the decline of the suit, as everyone knows, no one really wears suits anymore. And the reason that's popularly given is that we've given up on standards.

You know, nobody cares anymore. Everyone's lazy and a slob. I don't think that's actually true. What really, to understand the rise and decline of the suit, you have to go back to the 19th century. The rise of the suit was originally, the suit was originally considered a much more casual garment. People in high positions, such as finance, law, and government wore a long fitted garment known as a frock coat. Kind of like a tailcoat, I suppose, some people can imagine the length of the coat went way below like your butt.

I'm picturing like a Charles Dickens character, right? Yeah, like a Charles Dickens character, exactly. So that was considered a gentlemanly way of presenting yourself. And suits were for members of the working class. So like clerks, administrators, not for manual laborers. Like if you worked as a sailor or a miner or something, you wouldn't wear a suit. But if you worked as a clerk or administrator, a teacher, so on and so forth, you'd probably wear a suit.

And when you see the early stages of the suit, so for example, Keir Hardy, founder of the British Labour Party, he wore a suit to parliament for his first day as a member of parliament as a sign of solidarity to the working classes. And the British press was so shocked that they wrote about it. The parliamentary uniform at the time was the frock coat and a top hat, a silk top hat. And he wore a tweed suit and a flat cap. And the press wrote, a cloth cap and parliament. Which was kind of like, sort of analogous to like, Fetterman wearing a hoodie to Congress.

You know, it was like shocking. Yeah. So the change really happened around the turn of the 20th century where the rise of industrial capitalism, the class of people who benefited the most from the development of industrial capitalism was this kind of bourgeoisie class. And as their fortunes rose, the suit took on new meaning. It became a more prestigious garment.

And then younger people started to feel that the frock coat was kind of fuddy-duddy, kind of old-fashioned, and they wanted to look more modern. The suit had a kind of masculinity about it and kind of modernity about it. And so the suit was really started to... There were people wearing frock coats, even like 1910, 1920, but starting after that, most people wore suits. And the suit really lasted up until about the mid-century

when then you started to see it wane. And in the post-war era, my friend Bruce Boyer wrote a really wonderful book called Rebel Style that kind of presents this theory, is that the cultural wars of the post-war era were reflected in clothing. So you can think of the post-war cultural era as the man in the gray flannel suit versus the rocker rebel. The man in the gray flannel suit was basically all of the American vets that returned home

from the trenches of war in Europe. They came home. Let me just say you're basically describing the cultural conflict in Mad Men, which is a show I recently rewatched. So literally Don Draper is in that suit every day and he's constantly interacting with rockers and the sort of counterculture that's rising up.

And he was also a veteran on that show. I'm sorry, please continue, but left out to me. So the US veterans came home and the US government afforded them a free college education through the GI Bill. Many of those people took up the offer, went to college, and then adopted kind of bourgeoisie mores and norms and attitudes.

And so they became a version of the man in the gray flannel suit. They wore a suit, they got a corporate job, had two kids and a picket fence. And there were a lot of people who did not have those opportunities and they formed a certain kind of underclass in American society. Many of those people wore what's known as a zoot suit, which is like a very stylized, oversized volume of suit was worn as a kind of a fashionable thing of this day. If you watch the film Malcolm X, there's a scene where he goes, I think, into a jazz club and he's wearing, I believe, if I remember correctly, a red suit suit, which was kind of like a, yeah, just a very fashionable garment of the day.

So many of those people wore zoot suits, they wore kind of like work wear, they wore chambray shirts, they wore motorcycle jackets. And so this class of people presented a stylistic alternative to the man in the gray final suit. And as the post-war period marched on, young people became disillusioned with the establishment. And that's largely because, you know, you think of the 1960s, you have various freedom movements, you have the civil rights movement, you have the feminist movement, you have Stonewall, you have the anti-war protests. And over time, all of these kind of movements start to make young people not really want to be part of the establishment, especially after Watergate. Watergate made many people disillusioned with government. And so start

by the 1970s, exactly that scene that you're talking about of Don Draper in the suit is looking at these hippie kids. And that's the culture war. The suit returned briefly in the 1980s as kind of a backlash to hippies. There was a kind of greed is good period that was reflected in kind of fashion, if you will. But it really died then in the following decade with both business casual, the rise of business casual, which had been going on for a while anyway, but like 90s was really a lot of business casual. And then especially the tech industry boom and the rise of newly minted billionaires really killed the suit.

By the early 2000s, Mark Zuckerberg had turned hoodies and jeans not only as an alternative to the suit, but he made it a new status symbol. The hoodies and jeans uniform basically said, I don't care about formalities. I don't care about like all these I don't care about all these traditions. I am purely about meritocracy. I'm the whiz kid in my bedroom disrupting the economy. And I'm setting up this new system that stands opposed to traditional coat and tie

industries back east. And if you remember, all the way back to why the suit originally eclipsed the frock coat, it's basically the same story. Something that was originally considered very casual became a new status symbol because of shifts in the economy. And certainly, you know, I've seen you, Adam, wear tailored clothing very well. Thank you.

And that was, you know- I've also worn it very poorly. I've worn it very poorly as well. No, no, no, no, no, no, that's not true. I watched some old episodes, I'm like, holy shit. No, that's not true. That's not true, you're being modest. But I have seen you in tailored clothing and you look great.

And I started noticing you online in around the mid 2000s and obviously up to today. But starting around like mid, late 2000s, that was when it was a period when a lot of guys started to take an interest in tailored clothing. But that was kind of like a brief kind of like fashion moment, you know But that was kind of like a brief kind of like fashion moment. You know, that was not like a huge reversion

to everyone wearing suits. And I think the story of the rise and the decline of the suit is really about these kind of like, these developments in our political economy. Yeah, that is so fascinating. I mean, just saying from the beginning of the story that jumped out at me was the suit becoming popular during an age where the middle class became dominant

in society, in British and I assume American society as well, like, you know, we've been living in a world where the middle class is king. I mean, obviously the 1% does what they do, but culturally the middle class became dominant. And we had the, all of these societies became more democratized over time. Yes.

And so that became a status symbol, but it's also really fun watching the same as it ever was, Wheel of Progress, where you say that the Zuckerbergs of the world are now doing the same thing where they're, all right, we're all dressing down to show our individuality and that we don't stand on propriety and all these things. But now I feel like when I interact with tech people

and they're all wearing the same fucking hoodies and Allbirds or whatever they're wearing now, Allbirds was a couple of years ago, I'm sure they're onto some new goddamn fucking startup shoe. It's a uniform and they all look the same. And it's actually designed to enforce conformity. Like I'm sure if I went to Apple headquarters or wherever the hell Google is headquartered,

I would be stultifyingly bored by seeing all the same dudes in all the same outfit. And it's sort of fascinating to see that, you know, a uniform designed to show individuality become itself, you know, the same sort of constraining norm. I mean, nobody has to say, you must wear this like they do on Wall Street or at the Hollywood agencies today,

which are still places that force people to wear suits in the workplace, but it just social pressure makes people do the same thing. Yeah, there's a really good essay online. I feel bad for forgetting this person's last name, but his first name's Carlos, and I can't remember his last name, but the essay is titled Inside the Miratocracy.

And it's a person who worked at one of the big tech companies for a while as an engineer. And he wrote about how there is essentially an unspoken dress code in Silicon Valley that is enforced whether you like it or not. So he talks about how the tech industry likes to pretend that clothes don't matter and like we don't judge people on such superficial things.

But if you show up to a job interview in a suit, he says, according to him, that the disappointment will be evident on everyone's face because they assume that you don't understand the culture within the company and that you won't fit in. And this is sort of, I think this is kind of obvious to anyone if you just think about, we mirror people's talking habits.

There's a certain way of speaking at work that you might not speak at home. When you go to work, even if there's supposedly no dress code, you often end up feeling pressure to dress a certain way to show that you fit in. And it's sort of like when you start listening to punk music in the 80s or whatever and you start hanging around punk people, it's not like they gave you a book and said, here's our dress code. You kind of just like figured it out, you know?

Like you kind of realized, oh, this is the jacket, and this is like the general look. And then you figured out how to express yourself as an individual within those parameters. And that's what I mean by dress as a social language, that you end up speaking whether you like it or not. Yes. And you know, like you can pretend

that you don't care about clothing, but it's awfully strange that you dress a lot like, you know, the other people in your social group. Yeah, I mean, when I was, you know, just a working comedy writer at a website called College Humor, you know, this was in the, you know, 2011, 2012, there's a joke about, There was just a working comedy writer at a website called College Humor. This was in the 2011, 2012.

There's a joke about, we would all just say, oh yeah, I don't know, I just went to Uniqlo and bought some shirts, right? I don't really care about how I dress. And yet all comedy writers sort of dressed the same. Everybody wore the same plaid shirt, basically. I can still, and I know a lot of comedy writers who still dress that way.

And I now don't dress that way because I don't want to look as though I fit in too well with a bunch of other white male comedy writers. And this stuff has really drilled into us. Like, I think everyone's had the experience, or at least a lot of men have had the experience of, if you wear a jacket with lapels on the wrong day, people go, oh what, you're going to a wedding later?

And that's how you know that you, that's the dress code, right? That they just are, you're gonna get a comment that, oh, it is strange that you decided to wear that today. And I almost wonder if that is a huge part of what it means to dress tastefully or well, which is that you wanna communicate exactly the right thing about yourself.

Like, you know, I started, you're right that in the mid 2000s, I started taking more of an interest in dressing. It was around the time that I started performing more and I wanted to, you know, on stage as a standup comedian and then in videos, then eventually to make the show Adam Ruins Everything. And there was the Rise of the Menswear blog that you had

and Jesse Thorne's blog put this on, which I know you've written for for a long time. And it was just fun to learn about. But also I wanted to present myself a little bit better than the audience, you know? I wanted to like look slightly better and look like I know what's going on. But then when we did Adam Ruins Everything,

the idea was sort of like, let's take that a little bit too far. This is a character who reads way too many blogs and is overdressing for every occasion. A little bit too fussy. Tie clip, lapel pin, you know, a lot of patterns. Like, you know, it's just, he's taken a fit pic every single day

to post on, you know, r slash male fashion advice. Like he's just overdoing it. And that was the part of the communication of the character. He's taking a fit pic every single day to post on r slash male fashion advice. Like he's just overdoing it. And that was the part of the communication of the character. But if I were to dress like that now, I would again be overdoing it. And now when I try to dress to be on stage, I'm like, I wanna look better than the audience.

I wanna look like I know what I'm doing, but I also don't wanna look like I'm trying too hard. I don't wanna look like I'm mistressed for the occasion. Like it's a very subtle social like statement that I'm making and I wanna make just the right one. And that seems to be almost the essence of dressing well. Does that any of that track for you? I think that's true.

I think there's a few things in there of what does it mean to dress with good taste and that's a huge another topic. But then there's also an issue of dressing in a way that looks a little bit more natural and less contrived, I suppose, less forced, less of a put on. And that is, you know, that's kind of an idea that goes back to even Bu Brummel

who revolutionized Western dress. You know, famous quote that was something to the effect of, if John Bull turns around and looks at you, you're too fashionable or something like that. John Bull at the time was like a generic name for a stranger on the street. And yeah, I think there is kind of something to be said of like when you're putting together an outfit,

it does help to look like it was, if not effortless, then at least natural to you so that it doesn't look like the clothes are wearing you. I think that just kind of comes with, you know, time and comfort. But also, you know, like some of these, some of these ideas, I'm always careful of promoting because I, once again, I just think of clothes, an interest in clothes as a hobby and anything that get people into

what I feel is a fun hobby, I think it's great. And I just wouldn't want anyone to think that like, oh, I'm so scared that people are gonna think that I'm trying hard, that they never take that first step. And there is like, once you start trying, people are going to notice and you just have to be comfortable with it. Today's episode is brought to you by Alma. You know, let's face it.

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That's helloalma.com slash factually. consultation today. That's hello. ALMA.com slash factually. Well, I want to talk a little bit about men here because, uh, that fear of if I look like I'm trying too hard, people will notice and I'll get a comment is something that I think men feel a lot. I've felt throughout my entire life, and I have coached, after I learned how to dress myself a little bit better, I've had lots of men come to me and say,

hey, just how do I buy a suit? Friends of mine, how do I buy a suit? Where do I go? What do I do? Because they sort of have this feeling of like, oh, if I put any effort in, I will be criticized or attacked, or it's somehow not male,

or I don't feel comfortable doing it. And I find that really interesting that it's almost, you said earlier that fashion has been associated with women and with frivolity, but it's sort of like women's domain in a way, culturally. And I feel like a lot of men end up growing up like fashion or just clothing blind. They receive no training. They receive no fluency.

You know what I mean? No, no language skills. Right. And and to me, that's like a bummer. Like, like, I, I don't know. I've just, I've been around enough male friends of mine who seem like really almost catatonically, you know, unable to deal. And like, yeah, I'd love to hear you talk about that a little bit.

What caused that state of affairs? Well, as you know, I think there is the history of fashion being coded as frivolous and feminine. I also have a theory that after the trial of Oscar Wilde, it became more closely associated with homosexuality. So as many people know, Oscar Wilde was put on trial for homosexual acts. And Oscar Wilde was a man who was like very involved

in theater, he was like very involved in theater. He was like witty. He was known for these snappy comebacks. He also dressed with like, I mean he dressed wild. You read descriptions of him or you see like photos of him. He's wearing these like crazy plaid suits and like these giant feathers in his hat. And I think the trial of Oscar Wilde, fashion has always been kind of suspicious. Men who have been interested in fashion have always been viewed with some suspicion. But after the trial of Oscar Wilde, I think that cut the clearest line between why we think fashion

is associated with homosexuality, because so many of our gay stereotypes come after that trial. And I think after, during the 20th century, all of these stereotypes cast a long shadow. There's a really good article, an essay by Tom Wolfe called The Secret Vice, and it's about men who are obsessed with not just clothing, but bespoke tannery in particular. And he has a line in there says something to the effect of men would be rather seen with a porno mag in public than a clothing catalog. And obviously I think he was stretching it. This was written I think sometime in the 1970s. I think he was stretching it, but it wasn't far. I think people even till today

are somewhat worried about being associated with it. The other aspect that I think is that we are all often very self-conscious about how we're being perceived. There's a brilliant study, now I forget where it was done, but it was done at one of the Ivy League universities. And so this study, as many of your listeners know, these professors usually rope students in into their psychological experiments. So there was this study at one of these Ivy League universities where they put out a call

and said, you know, for five bucks or whatever, you can come and participate in this study and you will take an hour every time and then we'll give you whatever, this small amount of money. And they told all of these students to arrive at one specific location, all but one. One person was given a different location. And on that day, and at that time, all of these people arrived at one location, the one sole lone student, who was actually the target of the study, went to another location. When they arrived at that location, they opened the door and they find an empty classroom in which there's one professor.

And that professor says, I'm terribly sorry. We've changed the location of the study. It's now at this other room. You have to run down there very quickly because it's about to start. But before you go, you have to put on this t-shirt. And the t-shirt had a giant print of Barry Manilow's face. I thought this was very funny because this paper ended up getting published in an academic journal.

And there's a footnote at the bottom where they say this and the footnote emphasizes that Barry Manilow was considered very embarrassing to young people at the time, which I thought is such slander to Barry Manilow forever in academic kind of research. So this dude puts on his t-shirt and is running towards, you know, this like this room on the other side of this building, opens the door and you have to imagine yourself. Imagine you as that student. You open the door and the chairs are arranged in such a way that everyone's now facing you. So then you meekishly walk in, you try to find an empty seat, you take off your backpack and you sit down. And now the professor in that classroom says, you know what, I think you may have arrived too late. I'm terribly sorry. We're just not going to be able to include you. So now you have to pick up your backpack, walk out the door. And as you exit the door, there's a third principle of the study

there who's now surveying you. and this is where the actual experiment starts, they ask you a series of questions, one of which includes, how many people in there do you think noticed your Barry Manilow t-shirt, and you give some percentage. The principal inside the classroom asks the room, can you describe the clothes that that person wore?

And in every instance where they conducted a study, the person who was wearing the Barry Manilow t-shirt overestimated how many people noticed their t-shirts. And this ended up creating this term called the spotlight effect. And the spotlight effect is that our feelings anchor how we read other people. So when we're nervous,

we read certain things into other people. When we feel flustered, we read certain things to other people. And I think this also happens with clothing. If you wear something that feels unusual and you're already nervous about it and you go to the office or you go about your day and someone could pay you, honestly what they feel is a compliment. They're actually seeing

something nice like, oh, you're dressed up today, but you think it's, it's, they're kind of judging you. Like they're, you know, what do you mean by that? You know, of course you're not going to have like a prolonged conversation about it. So you just, you, you stepped up, you know, and then you kind of move on, but it kind of bothered you throughout the day. And that's only because you feel uncomfortable. It has nothing to do with what that person meant or intended. So I think there are, there are all of these kinds of weights, there's psychological kind of weight

of the spotlight effect. And then there's all of this history of fashion being considered frivolous and feminine. And then possibly people then questioning your gender and your sexuality. If you're a man who demonstrates that you're interested in fashion, which is why a lot of guys just end up giving up on it.

Yeah, and end up just wearing the uniform that everyone else in their office wears, or wearing the I don't care clothes, wearing the just whatever, I don't know, whatever, I just got some shit at Target who gives a shit what I wear, which communicates, that's its own set of communications, right? Like I think that's that's the sad bit about it is that if you

Never have the if you never try to communicate with other people using this you end up communicating something about yourself Without meaning to right? Yeah. Is that, yeah. I mean, your clothes communicate something whether you want to or not. So again, I've always strongly believed you should never judge a person's deeper, more important qualities based on their dress. But it is true that when you move through the world, your clothes do communicate something about you.

And this is often a way that you see expressed in professional spaces. So in academia, for example, there is more pressure on women to dress a certain way. First, in the humanities departments and the social science departments, people are more likely to put on certain types of clothes to communicate that they deserve the respect that their work kind of deserves. And then when you go into the hard sciences

where it's kind of taken as a given that the hard science, the physics professor must be brilliant versus someone in, I don't know, English or whatever. In the hard sciences, many people kind of don't feel those pressures. So they might arrive at work in like a t-shirt and like cargo shorts.

So I think these are kind of like ways that people use clothing to get the respect they deserve. But again, I strongly believe that you should never judge another person's character based on their dress, even if other people do judge you. Well, it's interesting, right? Because you say that you should never judge someone's character by their dress.

And yet by what someone chooses to wear, you could like, you do pick up things about them, right? And there is a sort of social analysis that happens when you look at another person, whether you want to or not, to some extent, am I right? I think it's fine to judge some things. Like if you wear a basketball jersey, I'm gonna assume you're a fan of the team.

And there are like, you know, like what we were talking about earlier, if you wear all birds, I'm gonna assume that you a fan of the team. And there are like, you know, like what we were talking about earlier, if you wear all birds, I'm gonna assume that you're middle-class, whether I'm right or wrong. I mean, that is like, you know, an assumption. But I don't think that you should read someone

as being smarter, more capable, more moral based on their dress. But I think it's, you know, like it is true that you sometimes look at someone, you know that they're middle-class. You can, you know, like it is true that you sometimes look at someone, you know that they're middle-class. You can, you know, some, historically what we were talking about earlier, when homosexuality was more taboo than it is today,

gay people often wore certain things to signal to other people their identity. These codes were kind of like, they kind of fell kind of under the radar, which led some people to believe that like, gay people have this kind of like sixth sense for, you know, gay people around them. There's a brilliant book called

Dawn We Now Are Gay Apparel by Sean Cole, who talks about the history of how people have used clothes to signal sexuality in ways that allowed them to pass as straight to the majority of the public, but also signal that they're gay. That's sort of like, kind of like, are you a friend of Dorothy kind of thing, but you know, by wearing a green carnation.

Yeah, that's wonderful. Talking about the modern conservative movement, which is often just something you write about on Twitter, and you have also written about, again, the DNC, the clothing of politics. I feel like you've picked up on certain trends in conservative male circles, at least in the political and media sphere.

And I'm curious what you've seen happen there, especially now that gender is such an important political talking point. Like what are those folks trying to express? Well, one of the things I sometimes express on my Twitter account is some of the people who are the most visible kind of figures for this return to masculinity movement or people who are lamenting, changing gender norms are often dressing in a way that used to have another kind of like form of gender panic around it.

So figures like Matt Walsh, for example, Matt Walsh wears these very short, trim sport coats, wears very skinny jeans. He basically dresses like an early 2000s kind of person who would have been labeled as a metrosexual. And the term metrosexual was originally coined by a gay writer, but was quickly picked up by the press and marketing people as a way to symbolize a kind of urban male figure and kind of question that person's

like gender and sexuality. Does someone suggest? Yeah, I mean, it was a statement about fashion, but sexual is in there. There's a connection to homosexuality. And I remember this was about 2004, I think this happened. So it's pretty early in, it's a number of years before gay marriage is legalized

that we have the acceptance of gay Americans we do today. So it was a very loaded phrase. It was a very loaded phrase. Guys were like, it was not considered something that you'd willingly want to be called. So what I find interesting is at the time, people who lived through that period will remember that there was a lot of anxiety over men

buying like specialized grooming products and like skin serums and wearing tight pants and all of these things. And the panic was like, are men becoming more feminine? Is like, is Western society about to crumble? And over time, the meaning of that dress has changed. I don't think that when people look at Matt Walsh today, they think metrosexual. They don't think he's possibly gay. They don't think he's slightly feminine. It's just that that's the kind of clothes that you buy if you just go to the store and

buy clothes because that's mainstream fashion. That's mainstream silhouettes, if you will. To me, it just demonstrates that all of the predictions in the early 2000s where people thought society was going to crumble, it turns out society was pretty fine. And even the people who are saying that they want to return to traditional modes of masculinity are wearing things that were previously considered kind of, you know, anxiety inducing, if you will. It's sort of like if 20 or 30 years from now, we have another wave of gender panic and the people who are most hard about returning to traditional gender

norms dress like Lil Nas X. It would be into them in 30 years from now, that's like normal. They're wearing assless chaps and they're on TV going like, we need real men to come back. Exactly, you know? So it's just, you know, like it sounds ridiculous now, but that to me, like, if you told me in the early 2000 that there would be this figure, I would say that's ridiculous. Yeah, that is really funny and strange.

And it's like this, I don't know, we have such a short cultural memory for clothes, but the interesting thing to me is the cultural language also extends really far through time. Like there are things that we think of as formal or, and I apologize, I'm jumping around a little bit in what I wanna ask you. This is something I thought of a little while ago,

but you were talking about how, you know, suits rose and fell, you know, over the course of a hundred years, and our opinions about them changed so much. And yet, there are also these long threads in the history of fashion that affect the way that we think about certain garments. I think a lot about threads that you've done

about, you know, the British aristocracy making a distinction between, you know, clothes you would wear in London versus clothes you would wear in the country. And in the country you're wearing, you know, hunting clothes, you're wearing tweeds and with patch pockets and stuff like that. And if I go buy a suit today at a suit supply in, you know, downtown LA or whatever,

clothes that look less formal are the ones that look more like, you know, a hundred year old British hunting wear for some reason. It still looks that way to me. And I, you know, I have a little bit more of, I know a little bit more about that history than your average person, but I do think you could put a couple of suits in front of people and say, hey, which one of these looks more like you would wear it to a red, you know,

a red carpet gala versus to something a little bit more, you know, a wedding in the woods. Yeah. Exactly. Yeah. Like what outfit would you wear to a business meeting where you're about to make a million dollar deal versus going to the pub. And people generally have, most people actually have a pretty good grasp. And I used to wonder about that, but now since my audience has grown on Twitter, sometimes I do these threads like, what do you think of, you know, what do you think these two things communicate or something? And you see like the majority of people, you know, they do get it

right. And I would love to one day have a conversation with a linguist because I think of it the same as language. We have slang, words sometimes change meaning depending on the context and time. But there is a general structure to the way we communicate that kind of lasts over time. And it's just, I think the same is true of clothes. There is still a general language that lasts, but there are kind of moments where new trends emerge,

just like slang. And then young people no longer say, you know, tubular or dude or whatever. I can't think of any. I can't think of some 90s term that young people have abandoned. But they've abandoned those terms in the same way they've abandoned, like, you know, slim fit. And they go back to a baggy fit because they don't want to dress like their parents. I think of it really, there's so many analogies

between the way we dress and the way we speak. Yeah, and I sometimes even feel that I sort of code switch in a way. Like you say, nobody wears suits. Well, I wear suits all the time, but I wear them at the correct event. Yeah. When I'm called upon to do so,

I don't wear them to the office every day like a Don Draper figure would have. And I also think that people who would never wear a suit, or at least, you know, men who would never wear a suit are missing out on the ability to, you know, present a certain version of themselves at a certain time to speak in a certain way, but in a completely different circumstance I would wear something different. But in a completely different circumstance, I would wear something

different. That's another connection to language, I think. Yeah, I don't think anyone has to wear a suit. But if you do take the time to develop a more intentional wardrobe, I would say. I think of it as just like eating. Like we all have to eat. We all have to wear clothes when we go outside. And if you have to do something every day, it's nicer to cook a tasty meal versus just boiling potatoes. And it's nicer to put on an outfit that you like

versus something that you either dislike or you're indifferent to. And just paying attention to that language makes it feel a little bit better. Yeah. And again, I think it's such a bummer that, so many men in our culture are not raised to be able to pay attention to that

language or to do so intentionally. Um, something else that I've always really been curious about though. Um, this is really my own curiosity. When I first started paying attention to men's clothes, there's a lot of emphasis placed on certain things, right? There's a lot of emphasis placed on fit on tailoring, you know, getting a bespoke suit made that's exactly made to your body. When you write about the stuff

that I know you're a real nerd about, it's like suit construction, it's how well it's done. If you're geeking out about shoes, it's like Goodyear welting and like handmade versus bench made and all this stuff, right? Like I subscribe to some of those subreddits, right? Like I read that stuff and I can like, you know, go to a shoe store and go, oh, this is a really good shoe.

And this one is like gonna fall apart in a couple of years, right? Now, and that stuff, you know, that's nerdy. You don't have to get into it, right? What I find really interesting is women's clothes has, have, you know, traditionally have completely different values. There's much less emphasis on bespoke tailoring, for example.

And I remember my, you know, my girlfriend for many years, we'd go shopping for shoes. And I was like, oh, you kind of can't do the same thing where you go, oh, this is a really well-made leather shoe that's going to last a long time. That's just like not one of the values that is as often expressed. Right. And I'm curious if you have any reason for that. Like why are certain things prioritized in high-end men's clothing or very tasteful men's clothing and other values in women's clothing?

Well, I would start off by saying that I know very little about women's wear, which is why I never really comment on it. But to kind of explore this topic, I think there are a few things at hand. One is that women's wear has much more quick moving trends. So there's less emphasis on something lasting for 10 or 20 years because the design is going to wear out before the construction. The other aspect is that I think men often approach clothing from this very technical

standpoint because it feels more comfortable than accepting the fact that you are into fashion, that you're self-fashioning. And so you treat it as like, this is logically the thing that I should buy because it is constructed in this way, made from these materials and will last me until I die, which actually like many people end up discarding these clothes well before they wear out because they find out it doesn't make them happy

and it doesn't fit their lifestyle or whatever. It's kind of funny. I think in the early... You're roasting me, Derek. You're roasting me. I do do this. Like, if I, you know, someone's like, this is a nice pair of boots.

You know, how much were they? Before I tell them the price, I'm gonna be like, oh, they're really well-made and they're gonna last a really long time. And like, these are like, they're actually really good though. I didn't just get them because they look cool. I got them because it's like explaining

why you got a really sick graphics card for your gaming PC. You know, I did my research. This is the best one. And that is like a male ego defense against looking to appearance driven. Yeah. The funny thing is, I think there were these kind of articles around like, I would say like maybe, I don't know, some somewhere like 2008, 2012, there were all these articles

about the differences between the way men and women shop for clothes. And I think actually it is good for whether you're a man or a woman or, you know, everybody to learn about what makes an item good in terms of construction. I think there is something to be said about like there is a certain way of making clothes that is often better. But it is true that at the end of the day, you have to like develop an eye for what looks good and then also an emotional antenna of like what makes you excited and feel happy. And that approach was poo-pooed in like around like 2010 and all these newspaper articles

of like, oh, women are so stupid for like only buying based on like, you know, whether it looks good and like if it makes them happy. But actually a lot of guys bought all of this like overbuilt stuff and it didn't actually make them happy. It didn't actually look good on them. So they ended up not wearing it. And then it becomes all for not the construction quality. The construction quality is important, but really the most important thing is whether does it look good? And is this something that you'll love wearing even like 10 to 20 years from now? If it's supposed to last that long, you should at least still reach for it and still feel

good in it. Yeah. You're describing the period when I was buying like a really crunchy raw denim jeans and trying to wear it on like an 85 degree humid day in New York and going like, oh, once I wear these for three years, like they'll break in and I'm not allowed to wash them and like all that shit. And like, I stopped wearing that stuff because it was, it felt bad. It felt bad on my crotch. I couldn't sit down in it, you know? And you know, now I've, you know, found a happy medium.

The funny thing about that is that I still love raw denim. The suits and tailor clothing, I should say specifically, and raw denim are like the two things I love the most. And I still love that like crunchy, uncomfortable feel. I recently bought a pair of these insanely uncomfortable fatigues, these cargo pants from a shop called Bracelens, which has a shop in Tokyo in London.

And when I put them on, they're so uncomfortable. And to me, that was like, that's like part of the enjoyment, like feeling them break in. Yeah, totally, totally perverse. You're not selling people on dressing well, if you're saying. No, I'm not. And the best part is how uncomfortable you are. That's the thing is that once you get really into it,

it's all stuff that is hard to obtain, hard to maintain, often looks ugly, and is uncomfortable, expensive, will get you comments that make you question yourself all the time. It's a huge pain in the ass, but I think if it's a hobby, then it's a hobby, and it's what I like

Yeah, I also just want to say just as we were talking about gender and clothing That something I want to add to what I said earlier Is that what I really find interesting about the differences between men and women's clothing is again part of how it works as language like one of the things that I think is I Really enjoy seeing is there are certain brands that will do sort of like menswear for women. Um, uh, and I think that's a look that is like really incredible and I really enjoy on women. I also enjoy, like, you know, once, uh, I also really enjoy that there's some wonderful like queer tailors that do, uh, you know, suits for, for queer folks, et cetera. Once you like, are like, all right, this is the sort of traditional

way that like menswear went, that became like, all right, this is the sort of traditional way that like menswear went, that became like, it becomes like another piece of language that like anybody can adopt in a way that is like, can be really interesting and vice versa. I just find it really interesting that those two branches of clothing diverged in this like really distinct way

in terms of what values they emphasize. Yeah, I think this is one of the most interesting times in clothing because there are so many different takes on that language. So many menswear guys that I know take inspiration from women's wear looks. And it may not even be that they're wearing women's wear, but they like are thinking of the combinations and, you know, different ways to wear things. A lot of my inspiration comes from how women wear clothing. And then as you know, there are queer tailors or people like doing this in different ways. To me, it's again, almost analogous to language. Noam Chomsky is famous for his phrase, colorless

green ideas sleep furiously, as an example of how a sentence can be grammatically correct, but semantically nonsensical. And so to me, there are grammar rules. There is a way of writing a sentence that says something, just as there is a way of putting together an outfit that says something. But then you have writers like E.E. Cummings that take great liberty with the way they construct a poem or the way some writers construct sentences.

And you can appreciate how slang can kind of come about through different groups. And that's also a way that dress can be much more interesting. It doesn't have to be this kind of like, I don't know, grammar school practice, if you will. And it rides the line between thinking of dress as like strict rules and there's only one way to do it. And then this kind of like free for all world where nothing matters. And again, as Chopsky points out, you can have a sentence that's grammatically correct, but still semantically nonsensical.

And that's sometimes why certain outfits fail. Like you can think blue goes with green, but then you combine them in certain ways and like the outfit still doesn't make any sense. Yeah, I'm thinking about your criticisms of the way Jordan Peterson dresses, the Canadian psychologist, I don't know, I don't even know how to describe his work at this point.

But he has taken to dressing in a, what I would call an outlandish fashion. And your critique of him is mostly that it's like the outfits are almost incoherent. Is that right? Like they don't make sense. Can you elaborate on that? Yeah, they just don't make any sense.

If you look at his outfits, you know, one outfit comes to mind where he was wearing, he had a special dinner jacket made. A dinner jacket is just another term for a tuxedo jacket, essentially. But he had a tuxedo jacket made with a black shawl collar and then this unique fabric that I think was like a Christian kind of like motif, which is fine. I think it's fine to make interesting kind of, or garments out of interesting materials. But then he would wear the dinner jacket with the long silver tie, I remember, in a white business shirt and these blue business slacks.

I can't remember what he wore for shoes, but maybe like loafers or something. And once you know a bit about the history of men's clothing, that combination just doesn't make any sense. You know, sometimes he would wear these outfits where the jacket is for hunting, the pants are for business meetings. And while it's fine to sometimes combine things that are different, um, you kind of just have to know how to do it essentially. Um, and his,

his outfits just don't show it with that kind of intentionality. And even if you don't know the specific history of clothing, your assertion is that the public, like in our cultural memory, we do have some sense of it, like some residual feeling about like, this has this history, this has that history. And so we feel the clash

and we feel that he has a bit of insensitivity to it. Is that right? Yeah. One of the things is that sometimes people ask, well, how did people dress? Like when they didn't know all of these rules. And going back to what we were discussing earlier, dress used to be connected to different subcultures.

And so those rules were known as you participated in that subculture. And that may have been that you were part of the British royal family. That could have been that you're a punk, that could have meant that you're a skater, that could have meant you're a hippie, whatever it is. And so the rules were known as a subcultural code that you would just know how a look came together.

We're at this moment where dress is increasingly disconnected from lifestyles and even possibly the person's identity. I mean, I see, for example, like hip hop kids dressing goth. I see people who look like they stepped out of bride's head revisited, but they're like actually super knowledgeable about street wear or whatever. And so when these kind of, when there's this disconnect and Jordan Pearson, to give an example,

wants to dress in a traditional manner, he exists outside of that social group, but then is then clumsily using their language. And all I'm saying is that in order to understand how to communicate that aesthetic clearly, you have to go back to the people that use that form of language. And you don't have to copy them exactly. I don't think you have to go back to the people that use that form of language, and you don't have to copy them exactly.

I don't think you have to dress like 1940s Cary Grant or whatever. But I think knowing the contours of that language allows you to express it in a way that's more coherent today. And in this specific case, most people know that the outfits don't make any sense, partly because the aesthetic of that classic tailored look

has been almost like preserved, like insects suspended in amber through mid-century films and TV shows and photographs. Like we know what that look is supposed to look like because we still have seen, like Cary Grant has been dead for a long time, but we all have seen photos of Cary Grant. So we know that aesthetic through cultural

kind of like artifacts. And I think that's why most people, when they look at that outfit, they know like, oh, that is not how you wear a suit or a dinner jacket. Right. You mentioned a lot of things in there, street wear, those sort of high class outfits of the past. I wanna talk about clothing in class a little bit.

I remember when I started reading all of these menswear blogs and things, there was a whole lot of, the style that a lot of folks were writing about was very, very connected to class. Ivy style was a thing that people were talking about a lot at the time. And I remember at the time going, yeah, okay, this stuff looks good.

I'm liking the photos, but wait, why would I wanna dress like a student who went to Harvard, you know, pre-desegregation? You know what I mean? Like literally a white elite kid. Why would I wanna dress that way? Now I understand when someone, you know, for instance, hip hop fashion, like, you know,

reclaims, you know, for instance, hip hop fashion, like, you know, reclaims, you know, high end white people clothes and et cetera. I get that sort of thing very clearly, but you know, I end up feeling just as like a, you know, white guy from a WASP background, you know, literally a Protestant, you know, I don't come from a background of wealth and class, but you know, demographically I come from the background.

I'm like, well, do I wanna present myself as though I go out on yachts on the weekend? Do I wanna dress like a Kennedy? It seems weird. And yet that stuff is integrally connected to fashion. So how do you think about class and clothes in that way? Well, as I've sometimes mentioned on my Twitter thread, How do you think about class and clothes in that way? Well, as I've sometimes mentioned on my Twitter thread, Pierre Boudreau wrote a wonderful book called Distinction,

where he lays out how we judge taste. And his theory is that, which I think is correct, is that our notion of good taste is often the habits and preferences of the ruling class. And in this specific case, that's essentially the class of white Anglo-Saxon prostitutes from families that stepped off the Mayflower. They had more of a kind of cultural influence prior to the 80s.

After the 1980s, I think, things shifted towards the Mark Zuckerberg types. And the reason why fashion is often so obsessed with a certain kind of taste is because it reflected a taste of people that ruled at least the US for much of the 20th century. I don't think you have to dress exactly like that, but it is interesting to me, I will have to say, how often that form of dress gets repackaged and presented in a different way. Amelie and Dora, for example, is a really popular, I guess, I don't know if you call them streetwear.

Streetwear is such a weird word nowadays, but they're a kind of like youngish brand that is often labeled streetwear. And for a while, although less so in recent collections, for a while, they were basically just like doing 1990s Ralph Lauren. In 1990s Ralph Lauren was basically repackaging Brooks Brothers and Brooks Brothers was basically the people that were dressing like, you know, like kind of blue-blooded wasps. And, but Amelie and Dorr has packaged it in a way that feels countercultural and kind of street wear just by who wears the clothes and how they're styled and all of these ways. And yeah, again, I think of it, you don't have to dress exactly

like that. You don't even have to be interested in any version of that kind of good taste, quote unquote, aesthetic. I mean, Rick Owens makes amazing collections and this stuff has absolutely zero to do with how John of Kennedy dressed. But it's a way for you to understand how taste is ends up getting classified and transmitted. I think when you think of it in terms of how it's connected to social class and structures in the political economy. Yeah, I mean, I guess my feeling about it is you've also written about how, for instance,

the Duke of Windsor was like incredibly influential. Literally, you know, a British member of the British Royal family is like dictating, made decisions that influence how I dress today, right? And part of me is resentful of that. I'm like, I shouldn't be taking my cues from some fucking guy who was just born, you know, in a position of wealth and privilege.

Like that seems stupid and wrong. And yet it's also the world that I live in and knowing that that's how it works allows me to, you know, again, have a certain amount of fluency in the way that I dress and communicate certain things in a way that is fun and comfortable and maybe, you know, attractive to people I would want to be attracted to me

or makes me look professional in certain circumstances or whatever. So I guess I feel both ways about it. There's just this, there's a strange thing to know that your taste is determined by the tastes of wealthy elites. It's just an odd reality, I suppose. That's true.

Although the history of 20th century dress is basically the switch from people with financial capital to people with cultural capital. So the Duke of Windsor was among the last of his kind in that he was a British royal and he popularized many fashions such as belted trousers, zip flies. He popularized a style of tailoring known as the drape cut

which was worn by Cary Grant and others. That was purely by the privilege of his position. He was a British roll. But over the 20th century, fashion influence switched from... I mean, those types of people still held a lot of influence, but it started to shift more towards people with cultural capital. So artists, musicians, countercultural types, so on and so forth. And I think when you, again, you

know, if you think of like spoken language, the way we speak is also formed by all of these different kinds of social factors. And that's just the kind of world that we live in. Yeah, I think if you think of, you think of dress in that way, it's much easier to discern how to put an outfit together than if you ignore it completely, essentially. Well, when thinking about how to put an outfit together, I think a lot of people are baffled by just figuring out how to dress. There is this perception that we live in an era

where you can dress in literally any way that you want and no one will bat an eye, which makes people feel a little bit at sea. And I think that's combined, especially, and especially for men, with an era in which all of our media about this has kind of collapsed. I mean, you know, I was literally in a bookstore the other day that sells magazines, and I was like,

let me see if I can find a fashion magazine that would be helpful to me. And all there was, was the sort of mass market magazines, which are like three pages long now and are just full of like editorial ads. And then the high fashion stuff, which I'm like, all these photos are beautiful, but like, you know, it's cool to look at,

but like, I'm not gonna wear, you know. A $4,000 Gucci bracelet or whatever. Yeah. Yeah. Or stuff that is so, but like, I'm not gonna wear, you know. A $4,000 Gucci bracelet or whatever. Yeah. Yeah, or stuff that is so, you know, like a drop crotch loin cloth or like whatever. Like this is a very cool idea that someone at the very high end had for a photo shoot, but it's not actually wearable clothing for me.

And so you are, you know, one of the things I think that made you catch is that, you know, you are simultaneously giving real historical information and advice on how to get your feet measured. And that is in oddly short supply. Even if you go to GQ.com, it's hard to find information like that. And so like, I'd love to hear first of all, a little bit more from you on like, what is fashion now?

Where are we at for, I guess, men specifically? What is happening? What is changing? And then where should people start if they are trying to dress with more intention? Well, this is one of the sad things. I think the reason why the suit died is because we had all of these freedom movements,

which are good. You can't imagine the kind of gender and sexual revolutions we've had while still putting men in suits and women in sundresses. But it has also posed this problem where as we give people more and more options on how to dress, it becomes more confusing on how to build a wardrobe. So if you're just a dude and you're facing out, you know, looking out into the market, there are now billions of options for even just like white button

up shirts, let alone like red and blue and pants and all these things. And then you're buying all of these clothes from specialty clothes. You're buying your pants from pant shops and shirts from shirt shops and you know, shoes from shoe shops and you're buying them online. They arrive at your door and you're supposed to figure out how to put together an outfit and as well as build a wardrobe, which I think is like also buying things online is its own problem because you buy and you're supposed to figure out how to put together an outfit and as well as build a wardrobe, which I think is like- And also buying things online is its own problem

because you buy something online and then it arrives and you're like, this looks horrible on me and now I have to return it. Like it's also disconnected us from the, we buy stuff without having tried it on, which I think makes it even more difficult. You don't even know how it feels or looks before you purchase it.

It's a really awful, awful kind of situation now to try to dress better. Cause there's so many languages, there are so many options. It's like you're buying stuff online. It's just very difficult. And I would note that the market has bifurcated into uber high-end, like thousand dollar shirt

and then two dollar shirt. You know, the middle has like totally collapsed. So it is difficult. I think the other thing I would notice that a big change is that men who used to be interested in clothes used to be able to turn to like fashion magazines as you've noted, but many of those fashion magazines have kind of abandoned that role partly because they can't compete with the internet. Like they just assume that you don't need another editorial about how to tie a tie because you can go to YouTube. But at the same time, the Internet has made it more difficult to find this information.

There used to be blogs and forums, but now it's all like paid sub stacks and closed off Discord channels. And you have to find the right accounts on Instagram. It's very difficult to get this information now. I would say if you're a guy who's trying to build a better wardrobe, it absolutely helps to first start with thinking of clothes as a social language. And although I hate to be prescriptive, because I think there, there are just way too many, you know, ways to build a wardrobe and there's no single essential.

If you're going out and just starting to build a wardrobe, it does help to get some basic button-up shirts in a simple color like white or light blue, some nicer t-shirts, a couple of jackets, very simple jackets like a field field jacket, maybe denim trucker jacket, maybe a Navy sport coat if you think you're gonna wear tailored clothing. Buy three pairs of shoes, buy things that are really basic, not because those are the items that you will wear for the rest of your life, but because these are items

that allow you to explore your taste. So that when you go out and you happen to come across a really cool jacket, you can buy it, bring it home, and then you have the things in your wardrobe that allow you to see if this thing can work. And that ends up being a basic button-up shirt, a t-shirt, a pair of jeans, or a pair of tailored trousers. And you can see, does this actually work? And through trial and error, as you think of clothes as social language, you can then find what works for you. Figure out the stores and the brands that work for you.

Find their Instagram accounts. Go to the Tags section of the Instagram account. See how people are wearing these clothes. Follow the ones that you think are stylish. And then through those accounts, you'll find out about other brands. Let's say you have decided that you really want to dress preppy or whatever. So you discover a store called Sid Mashburn and then you follow Sid Mashburn and the people that wear Sid Mashburn.

Then you discover a store called whatever, like the Armory or whatever. Through all of this, you can then discover new shops. You can follow people, you can save photos of outfits that you like. And I think over time, through shopping slowly, don't buy a full bespoke Taylor wardrobe within the first year. Through shopping slowly, experimenting and finding your own taste, I think that is probably the best way to do it. As long as you keep in mind of thinking of this as social language and not just a random amalgamation of like cool trendy things.

Yeah. And that's a beautiful piece of advice to start from it, from a place of social language, because I think that one of the things that makes me happiest about having a wardrobe that I feel pretty good about now, it's taken me a couple of decades, but I feel like much more comfortable than I used to, is that when I go to an occasion, I can think, okay, what kind of occasion is this? What, you know, what is this?

Is it in the day? Is it at night? Are we gonna, is it gonna get messy at all? Is it very formal? And I can put together an outfit that like broadly matches that. And I might only have one outfit that fits, you know, whatever this is.

Like I really only have one thing that I wear to like a black tie event when I have to do that for some Hollywood reason. I really only have two or three things I would wear to like a summer pool party or whatever. But it feels really good to go, what am I trying to communicate in this setting and let me dress to meet that?

You know, do I want to be a little bit more dressed up than everybody else? Do I I wanna be a little bit more dressed up than everybody else? Do I wanna be a little bit more dressed down than everybody else, et cetera. That has enabled me to feel more comfortable in those settings rather than less. And I think that requires just taking the leap a little bit. Like again, I know so many men who are like,

they don't own a suit that fits because they have this like who me feeling like, oh, who am I to, to, you know, get a little dressed up, like, won't people stop and stare? It's like, no, if you can actually establish comfort with that piece of language, right? And like just get used to it, then you will feel comfortable in a situation in which you might otherwise feel uncomfortable. And it doesn't take that much. It takes getting one, you know, one all purpose suit that, that fits you and that you feel okay.

And it's just like learning a little bit to do that. And so I, that's what I always try to encourage, you know, men in my life who are feeling nervous about it is like, get yourself measured, man. Like it's okay to get something tailored. Like you deserve it and you'll feel better once you do it. You know? Yeah, I think the biggest way you could dress better

is just by paying attention to culture, both historical and contemporary. And my guess is that anyone listening to your podcast is already like steps ahead in that category. If you watch films, TV shows, you're probably already cued in into the social language of clothes because, you know, those costume designers are using clothes

to communicate something about the character. You already know that because you watch those shows. So, yeah, go figure out that language, figure out the kind of how you want to present yourself, and then go shop slowly. Find, you know, a couple of basic pieces and then go experiment, you know. Find, if you want to dress more rugged way, buy a pair of, you know, like nicer raw denim jeans, or you buy a pair of double-knee car hearts, if you buy a pair of, you know, like nicer raw denim jeans, or you buy a pair of double knee car hearts, if you buy a chambray shirt. And then, you know, see if you wear it for a while, see if it makes you feel good.

And if it does, then, you know, explore that kind of aesthetic a little bit more. And also just feel comfortable with the fact that, you know, people are probably going to like notice that you're dressing better and they're probably going to comment on it. But it's not, you know, it's not always a judgmental bad thing. It's just, people talk. Yeah, and look, you gotta use that. People are gonna talk no matter what you do. So you might as well try to give them a reason

to talk about you in a good reason. Go, oh, he's dressing a little better, good for him. Or dressing a little more intentionally or dressing a little more interestingly. Yeah. Well, Derek, that's wonderful advice. I could talk to you for a thousand years, but we should probably let you go.

Where can people find you on the internet? And yeah, especially if they wanna use you as a resource for learning more about clothing and culture, where can they find you? So I think at this point, more people know me from my Twitter account than my writing elsewhere. So find you? So I think at this point, more people know me from my Twitter account than my writing elsewhere. So you can find me on Twitter at the handle

Dye Workwear, D-I-E, and then work, and then wear. But I also have a website under that name, DyeWorkwear.com. And at the same time, most of my service writing, meaning like articles on how to dress better, are at a site called Put This On, which you can find at PutThisOn.com. And at a site called Put This On, which you can find at putthison.com. And when you go to Put This On,

there's a link at the very top that says start here. Just click start here and you'll find a bunch of articles. Use the navigation bar and you can find some more articles on how to build a wardrobe. And I have bought many things over the years because you've recommended them and always loved them. You have wonderful taste. You always steer people in the right direction.

So I can't thank you enough for coming on the show, man. It's been really great to have you. It's great to be on the show. Thank you so much for having me. Well, thank you once again to Derek Guy for coming on the show. If you love that conversation and you wanna support the show,

head to patreon.com slash Adam Conover. Five bucks a month gets you every episode of the show ad free for 15 bucks a month. I will read your name in the credits of this podcast and put it in the credits of every single one of my video monologues on YouTube. This week I want to thank Michael Lurer, Cam, Darren Kay, Steven Volcano, Angelina Montoya, Matthew Reimer, Ethan Barak, Pellette, Gabriel Guerra, Ed, Ruben Salvang-Veilen, and a bunch of other fine folks as well. Head to patreon.com slash Adam Conover if you'd like to join them.

Once again, if you wanna come see me do standup comedy in San Francisco, Austin, Texas, Portland, Seattle, Boston, Providence, Chicago, Batavia, Illinois, head to adamconover.net for all of my tickets. I also wanna thank my producers, Tony Wilson and Sam Roudman, everybody here at HeadGum for making the show possible. Until next week, we'll see you next time on Factually. I don't know anything.

That was a HeadGum podcast.