The Daily - Sunday Special: The Fashion Episode

Episode Date: September 28, 2025

This month kicked off the big four fashion weeks: New York, London, Milan and Paris. Each year, designers, brands, influencers and celebrities flock to these events to see and be seen.On today’s episode, Gilbert sits down with Stella Bugbee and Jacob Gallagher, two of The Times’s foremost style experts and veterans of the fashion week circuit, to discuss clothes. They talk about what fashion week means in the frenetic fashion ecosystem of 2025, and they answer some listener questions about how to cultivate a personal style. On Today’s Episode:Stella Bugbee, the Styles editor for The New York Times.Jacob Gallagher, a fashion reporter for The New York Times.Background Reading:Armani’s Influence on New York Fashion WeekPhoto: Simbarashe Cha Subscribe today at nytimes.com/podcasts or on Apple Podcasts and Spotify. You can also subscribe via your favorite podcast app here https://www.nytimes.com/activate-access/audio?source=podcatcher. For more podcasts and narrated articles, download The New York Times app at nytimes.com/app.

Welcome to the Daily Sunday special. I'm Gilbert Cruz, the editor of the New York Times book review, and every week I'm here with my colleagues. We're talking about music and movies and books and TV, just all sorts of fun stuff. Today, we're talking about fashion. This month kicked off the big four fashion weeks, New York, London, Milan, and Paris. and if you've ever seen even a single photo from one of these runways, I think you know that those clothes bear little resemblance to what we wear on a daily basis. But those clothes and those events are still important and influential in many ways.

I want to know how, and today we're going to talk about that. And we're also going to answer some of your questions about personal style. With me today are two of my colleagues who cover fashion for the Times, Stella Bugby, the editor of our styles desk. Hello, Stella. Hello, Gilbert. Also here is Jacob Gallagher, who is one of our fashion reporters who goes to a lot of Fashion Week events.

Hello, Jacob. Hi, Gilbert. Hi. Okay, so I feel like I have to fess up straight away. Maybe you already know this based on what I wear around the office, but I don't feel like a particularly fashionable person. I don't follow the world of fashion. I don't think about it a ton.

Not because I don't think it's important, but because it seems kind of impenetrable to me. It's a little like sports sometimes. There's so many names to remember, so many designers. I'm hoping that we can have a conversation that sort of unlocks that. But I want to go way back first. I want to ask each of you,

when you think you first understood that fashion was not only important, but it's actually something that you wanted to spend your time thinking about. We're all pointing it. I think what makes fashion interesting to me is that it is it's about how we like to be perceived out in the world and the messages that we like to send and it's one way that we can decode the world neatly and easily or at least that's the hope right you you pick the clothes you pick to communicate sort of how you think you stand in the world if you can I think I was very aware of that growing up in Washington, D.C., where what you wear is very coated to where you fit into the world. And as a very little child, I just remember thinking, like, oh, it's

very easy to tell which group everybody is a part of. There were the suits, the punks, the soccer moms, just these tribes of style choices that people would make. It had nothing to do with high fashion. As a young, young child, I wasn't, you know, aware of trends or anything like that. But I was very aware in the way people use fashion to display their values in the world. Yeah, Gilbert, I'll maybe ask you to not use fashion as much as clothes. Like, I'm sure a lot of listeners make that same distinction, but to me, like, what we do is cover clothes. Like, I think, and fashion is a part of that, like high fashion as you're perceiving it on the runway is certainly part of that. But, like, what we talk about is just the broad universe landscape of clothes.

And so, like, I also grew up. I grew up right outside D.C., and I grew up in kind of the skateboarding, hardcore punk world. And that is a very, you know, aesthetically driven space. It's very tribal. How you dress dictates, you know, what you're into or who you're into. And I think that was where the awareness came in for me. Like, I have a cousin who is from the Bay Area, which was its own punk scene. And I will always remember, in the way you always look up to your older cousins,

he had a hoodie that he never washed, and it was disgusting. But I thought it was the coolest thing on earth, because it was, like, from this band that he loved and he was really into that I didn't know of because they were from the Bay Area. And that, I just remember the fact that it felt like that sweatshirt had something that made it greater. And the fact that a piece of clothing and cotton stitched together could take on something, like that, that registered with me pretty early.

And I would say to maybe try to answer your question in, like, the high fashion world, the first piece of high fashion I bought were a pair of Junio Watanabe jeans that I bought what I was like, I want to say 20, and I had just moved to, I transferred colleges, I was in New York, I was working retail, and I saved up for these jeans, and I really, they looked like what you'd put on a scarecrow, like out in the... Put on your farm. They were like really patched. Yeah, it was like they should have come with a packet of straw.

But they, to me, they felt, and I hate saying this word now because it's so cringe, but they felt very punk. They felt like the high fashion version of what I grew up looking at and believing in and wanting to emulate. And I still have them. I refuse to get rid of them. They are not like way, way too small, but they're so prized to me still. I think what you're getting at is one of my favorite terms, which is the narcissism of small differences, right? It's like this idea that you're going to notice that somehow my shirt is different than somebody else's shirt because you're going to be clued in to the secret messages that Junior Watanabe jeans might, you know, send out to the people who know what those things are.

That's kind of what makes fashion sort of fun. Absolutely. What happened to your cousin's sweatshirt? Oh, man, I'd have to ask him. He definitely did watch it at some point, or it's just disintegrated. It's now in a landfill out near Benicia, California. He never washed it. He never washed it.

Well, you know, I mean, also, like, there was a time where this is a total tangent, but in, like, clothing, you know, the whole thing was to never wash your jeans, and they could, you know, eventually walk out the door on their own. But they, I tried to never do that, but I wonder if he was just ahead of the curve, maybe, on the raw denim movement a little bit. I feel like we all had that cousin. Oh, totally. That you looked up to you totally.

It's always a cousin. It's never a sibling, you know. As we speak, New York Fashion Week has ended. Stella, you are shortly going to head over to Paris Fashion Week. Is that correct? I am, yes. So speaking for myself, I have little idea what goes on at these events. I see videos.

I see photos. I imagine various celebrities sitting in various places and watching models walk down the runway. But I actually don't know what any of that means. I don't understand what's happening in the room. I would love for you to decode it for me a little bit if you can as someone who's been to maybe more than a few of these.

Yes. I don't think that I understood before I started going to fashion shows exactly what the purpose of fashion shows were. They are both to display new ideas for that season, or for the coming opposite season. So if it's fall,

we're looking at spring of the following year. If it's spring, you're looking at fall. And the show is supposed to preview for editors and members of the press, as well as buyers for major department stores and smaller stores, you know, what's going to be available. And so the buyers will go to the show, and then they will do an appointment after the show and pick which things they're going to bring into their stores. The editors will go to the show, and they will ostensibly decide which looks they're going to photograph in the pages of their magazines. That was how it used to work.

And that's pretty much still the format that we all follow. Am I missing anything, Jacob? Well, I would say I think it's important to parse out that the buyer interaction has in many cases, like, that's withered, I would say. Like, because a lot of, as you kind of alluded to, actually, Gilbert, like, for some brands, what they show is purely conceptual. It will never be shown to buyers. It will never be purchased. It will never land in stores. I think people focus maybe a little too much on that aspect, but there is no denying that the purpose of it, I think, is now more as marketing exercise than as a way to drum up interest for the commercial side of your business or to get, you know, to try to offer catnip to those buyers.

I think now it's like the event itself is the marketing end. And you see that in like reports about how much like marketing dollars these shows acquire. wait to and what have you, and that's why they invite celebrity and all that. But I think it still functions the same as, like, a member of the press in a way. You're still looking at it trying to dissect, like, what this might mean for the broader market. Yeah, like, what are the trends going to be? I think that's a big question coming out of each season. That, at least traditionally, has been.

Traditionally. I wouldn't say that it's so predictive. Yeah, I think that's right. I think, like, the glamour that you're seeing, if I can kind of try to bring you in the room. Please do. The glamour that you're seeing is really not what we're experiencing. It's like if you've ever waited for the bus or if you've ever been at a concert and you've been like, why will this band just not go on already?

That's what being at a fashion show feels like a lot of the time. You get there and you sit there and you're like, okay, it's this like performative ritual of if the show's at one, it will actually begin at 140. or when the last celebrity that they have been waiting on finally arrives. And that can be... And it will last 10 minutes

and then you will be herded back out of the time. Yes. What are you doing in those 45 minutes? Are you looking around? Are you... I play Spelling Bee by the New York Times. No, like any good reporter, I'm getting up and I'm going to talk

to whatever celebrity is there. And sometimes they're interesting and a lot of times they are the same celebrity that you've already seen three to five to seven times that week because, you know, like the season that Chapel Rhone got popular, like, it was like she arrived in Paris and her people were like, we'll have her go to every show possible. And she was at all these shows back to back to back. And part of that is like image building for them.

And part of that, I don't know what brand deals Chapel Rhone has or what she's fostering, but part of that is that eventually that relationship with the brand might result in a endorsement deal that could be very lucrative for them. So, especially on the men's side, like, you know, the NBA's off-season, you'll see a lot of basketball players just suddenly show up at these shows, and they're going to

like, Zenya, then they'll be at, you know, the Canali presentation. Then they might show up at Prada, and you're like, why, how did you end up just like, who's making your schedule? But in a way, that becomes its own trend. Oh, yeah, absolutely. It's like almost more interesting to see who's at the show on the celebrity

side, on the VIP side, because It's a way to see, like, culturally, who's mattering to these big brands. What are you seeing in the room, Stella? What are you looking for? I mean, what I'm looking for in a show is something surprising, something directional, something that changes my mind about the brand even. You know, if I often go into a show with an expectation from a certain brand, and when they surprise me, I'm always delighted.

It's like, oh, I've never seen Tori Birch do something so interesting. Yeah, can you tell me? something that falls into this category? I mean, you don't have, yeah, you don't have those moments very often. And when they happen, it's like, oh, all this waiting, all this stress was worth it, because that was magic. You know, that felt really exciting. And I can imagine that changing the way that women are going to wear their coats or something.

You know, I mean, we have those moments few and far between. But I remember, for example, you know, there'll be a designer like Eddie Sillard. Lamein, who is a very, you know, controversial type of guy. Polarizing? Polarizing, perfect word. Like, personally polarizing or professionally polarizing? Yeah, like, and he's been at the helm of several brands. But, you know, sometimes you'll be sitting there and you'll have an experience like I did in, I don't know, this is more than 10 years ago when he took over St. Laurent.

And everybody in the audience hated it so much. And I remember sitting there thinking, I don't know, this is kind of fun. It's kind of good. and maybe it's a little provocative and rather than, for example, being swept up in the energy of disliking it, I was sort of like sitting there allowing myself to think whether I was about to have an independent reaction

to this thing and going back to my hotel room afterward and writing that I liked it and then feeling like, uh-oh, I'm going to be at odds with the prevailing attitude about this particular show. And that kind of thing is very fun. What was their look? Oh, that runway was just a, bunch of leather mini-dress, which, you know, everybody was like, oh, those could be from

Hot Topic. And I sort of had a different feeling about it. And just that willingness to challenge my own expectations and then also perhaps be at odds with my peers. And it's kind of fun to have those moments. You know, I often get them at Prada. Like, you'll sit there and she'll send something out that's so wild and different and crazy, something like you've never seen, and you have to decide, is the reaction I'm having negative? Is it positive? Is it, is it positive that it's negative? It sounds silly, but that's what makes it fun. That's what makes it glamorous. That's what makes the sport of it engaging year after year after year. Jacob, do you remember a moment at a show where you said to yourself, I'm seeing something that

feels unique, different, I'm having a genuine aesthetic or emotional reaction to it? When the whole experience is calibrated just right. It's like the, it's still, to me, I feel corny saying this. It's still like the greatest thing to get to witness, I think. Like, there's a couple of Prada shows from back when I remember there was one season where the space was like a ship and we were sat like sunken looking up at the runway. And the whole, the collection was this kind of nautical shipwrecky feeling. to it and I remember sitting there and I was like this is so incredible and I just want like this

p coat and I remember thinking like I still try to find this p go from this collection and had like a denim strip on the sleeve but it was incredibly um like it felt like being in theater kind of like you were in an immersive theater experience that you could then shop from which is so cool as as a way to break down what a show is yeah I think I'm not shopping so much as wanting to have my perspective changed around my own desires and my own idea of the way that someone can look. So, for example, Valenciaga, I have never bought an item from Demna, who designed Balenciaga for all these years. But I remember sitting in his shows, like his early shows in Paris and thinking,

This is a totally different way of presenting a body of, you know, interpreting modernity. And those kinds of thoughts, like whether or not I was actually going to buy them was less important to me. It was more that I had never seen anything like this before. And that's kind of thrilling in and of itself. So, yeah, I should say, like, as a critic, like the times where I'm sat there being like, oh, I want to buy something, very, very few and far between. Right. But that piquot. But that piquot still does rattle in my brain.

But, you know, I think there have been a number of shows, you know, he's now at Dior. But Jonathan Anderson, on the men's side in particular, to me, has been very, very good at that. He was at Luevae for a number of years. But he would do these shows, and you would kind of see the way he was thinking about the male body proportionally in particular. Like, I really remember this one show where he showed these pants that were, like, sad. at the rib cage and they were sparkly, but they were shown with otherwise conservative items, you know, dark blazers and buttoned up shirts. And I just sat there smiling and was like, this is actually new.

This has no applicability to how anyone will or probably should dress. But what a cool way to rethink where a pants should sit. And maybe that will have impact to make people think differently about how their pants sit, not to that dramatic scale. Sure. But, like, certainly you could see him saying, okay, I'm going to plant the flag here. Now it's up to you guys to see how far you want to go to catch up to me.

That's a great transition because I feel like what you are both talking about is an aesthetic experience in some way that you're having there, right? You're thinking about fabrics. You're thinking about looks. You're thinking about moments of extremity, maybe. But how is that influencing the way I wear my jacket on the street? You know, how are the high pants influencing? Maybe not these pants, which are the most boring? J crew pans you could possibly find, but I love the way they feel on me.

How are those affecting the way people wear pants? Well, you know, we brought up, Stella brought up Eddie Slimane earlier, and it's like, that's probably the last like real, I mean, correct me if I'm wrong, but to me, that's like what he did at Saint Laurent was the last time that the runway had like a movement-wide impact on how people dressed in the mainstream. You had like Eddie Slimane and then Tom Brown both pushing very strong. shrunken suiting but then that really did like that's the reason why like j crew ended up doing their like slimmer suit like that did have a direct trickle-down effect today listen it's it's

harder to see for sure i think you have to really be looking at the corners and and and squinting to see the impact at times but it's there like i i think well i would say something much like slightly more controversial, which is that it's always trickled up more than we give it credit for. So, yes, designers, they're synthesizing the moment. They're looking around the world. They're putting it through their filter and they're interpreting through it sort of high fashion lens. But these trends probably bubble up as much from Jacob's cousin's dirty sweatshirt as they do from music, communities, or, you know, subcultures of all kinds. And there's, I don't think that historically we've given that enough credit for the way that people like yourself dress or people just like just regular people dress. You know, what's fun about looking at fashion historically is that you can identify time periods, very sort of succinctly, like based on what people were wearing. I don't know that that's so easy to do now. We live in a kind of like post-consensus, post-trend world.

I just, like, you're wearing something that you could have been wearing five years ago. You're wearing something probably that you'll be wearing in five years from now. Absolutely. People always ask both of us, what are the trends for the season? What's in? What are the trends? And it's really hard to answer that now because I don't think that you could reasonably say there is one or there are even five. Yes, there may be a lot of lace on the runway or something like that.

But it doesn't necessarily mean that there's going to be a lace trend. It doesn't work that way anymore. But I also think that, like, the way that high fashion works, the way that luxury fashion works now, it has to be broadly palatable. And what I mean by that is these corporations that own these smaller fashion labels, your Louis Vuittons, your Dior's, your St. Laurent's, your Valenciagas, they have to be globally successful.

And when you are operating at that big of a scale and you have to continue to generate revenue at an incredible clip, you don't offer as revolutionary of ideas within the store. And that's true both for, I think, the huge companies as well as, like, you know, your big mainstream fashion labels,

your, you know, Levi's, your gaps, your uniclose to an extent. And so you kind of have to keep giving the consumer what they're buying into already. And so it does become harder and harder to, I think, revolutionize that consumer and create excitement and have people really believe they need to get behind that.

I feel like there are so many analogs here between clothing and other sorts of culture, other kinds of pop culture, which is, you know, the corporations, companies say, we know there's a mass audience out there for these type of movies or these type of TV shows. Therefore, that is the thing we need to cater to. We need to make the most palatable form of it

because we are here to make money and high forms of art or experimentation maybe is not the thing that we are going to invest in. Well, I would also say, for me, when I was growing up, like the way I dressed was a reflection of the subculture that I was into, I think now the way kids dress in a lot of ways is a reflection of the clothes they're into,

if that makes any sense. Like, that, like, the clothes themselves are what people are interested in and what they're pulling from, and they're very removed from their original subcultural context. So that ends up resulting in, like, you're seeing this weird feedback loop right now where, like, kids on the street, kids, we're using kids very loosely. Let's say, like, 20-something people on the street, teenagers are dressing very, like, 90s, like the baggy pant crop top thing. And then that, I think, is then feeding back into fashion. And you're seeing designers then try to give that directly to that audience. So they're trying basically to make money by pulling from how these kids are dressing. I think we're – I like to call my kids who are Gen Z, like, Gen Z chaos fashion.

It's just – So it has – Have you officially branded this? Is this? With them, yes. I love how chaotic they are. They're truly chaotic. Like there's no – I look at the choice.

they make, and I'm like, I don't understand what's informing this. And I don't think they do. And I think that that's what I mean when I say post-consensus. But I keep thinking about Normcore, which was a little over 10 years ago, a pretty big movement that was, I think, a rejection of individuality. And that didn't come from fashion, but it was expressed often through fashion, which is just this, everything is generic, and you're one of seven billion, and that has been hard to shake. Although when I talk about Gen Z Chaos style, I think that that is the first time we're seeing kind of a rejection of Normcore, which I think has been, Normcore being the most prevailing aesthetic that we've seen in the last 10 years, and whether that's in minimalist

clothing or minimalist interiors or millennial pink or any of these big pervading aesthetics that that have like really changed interior design or have changed car design or shoe design or, you know, all of those things were related to that. Now I think we're seeing a more eclectic rejection of that desire to be anonymous. People are, I think, finding their individuality again a little bit. Okay. On that point, let's take a break. And when we come back, you all are going to answer some listener questions. A few weeks ago, we did a call out, and we asked listeners to send us their personal style questions, and we got so many responses. Thank you to everyone who submitted a question. Obviously, we can't ask or answer them all, so I'm just going to put a few to Stella and Jacob and see what we get. Are you guys ready?

Sure. Yep. So as I, so many questions, as I said. And as I read through many of the questions, I saw that something that a lot of people had on their minds is how to dress for their age. People in their 60s, 70s, people in their 80s, but also listeners that were much younger than that. And this first one is from Paul. He lives in Rostock, Germany. Paul asks, I've been trying to find a more modern adult style for a while now.

since I'm still wearing a similar style to the one I've been wearing since high school. I believe Paul is in his late 20s. Why is that and how can I change that? I can answer the why easier than the how, I think. The why is that is because basically there's very little societal pressure today to dress in an adult manner, depending on your career. But, you know, I think there is not the same pipeline of like you graduate school, you get a mature wardrobe as you move into the workforce. You don't need that anymore based on, I would say,

the withering of dress codes in the corporate world. It's very hard as a result. I feel for Paul, like I do understand that. Like, it's hard to try to then dress in a way that feels better without feeling, like, risky. I get that tension. I feel like we need to go back to the, to the fundamental question.

And you said we got tons of questions about how to dress your age. And, you know, pulling back on that, it's so hard to age, period. We have, like, a ton of things to navigate psychologically around those questions. You know, it's not just clothing. It's your body changes.

It's your feeling about others change. It's your feeling about your authority in the world changes. How do you reflect that with your clothing? That gets at the very most difficult question about fashion, period. So it's not surprising to me that so many readers would ask, like, how do I dress my age? Because how do I talk my age? How do I feel my age? You know, I might feel a lot younger than I see or that I look.

So I would say it's probably okay for him to dress like he did when he was 20, as long as it's okay for him socially. But if it doesn't line up with how he feels as a person, he's going to have to actually spend some time thinking about how he feels as a person and then he'll figure out how to dress. I think we think that clothes will answer those questions for us, but in fact we have to answer those questions and then go out and find the clothes that match our feelings about ourselves. And, you know, that actually evolves fairly frequently as we age. And that's why you're getting questions from people in their 80s, 70s, 60s, and lower is that, like, we're always trying to navigate this problem. Well, I think a lot of people don't want to, again, dress like they're trying to be 25 when they're in their 40s, or they don't want to try too hard to look cool, even though they want to feel good in their clothing. One thing that I keep saying and thinking is that it is almost impossible to escape the moment in which you were forged. You cannot quite shake that, whether you're a boomer, whether you're a Gen X, whether you're a Gen X, whether you're Gen Z.

Like, it just will be there. And there's something in there that you can't quite fight. And that's okay. Stella, I went to a Catholic All Boys high school, and I still dressed that way. I think I locked it in when I was 16 years old. that was a really beautiful answer. I thought that was really eloquent. Tell me I'm wrong.

No, no, I think that you are absolutely right. But I'm trying to think of how materially to help here. And what I would say is already asking the question clearly indicates that there's something that when Paul and people like Paul look in the mirror, they think I'm dissatisfied with this. This seems off of who I am or who I'm trying to be. And what I would say is try to then stand there and figure out maybe what part of what you're wearing makes you feel that the most and begin there. Like if it is that you're still wearing the same exact chinos you wore in high school or the same exact sort of Catholic school buttoned up, if you will, and that that is pulling you too far backwards or too far to that time that you want to pull out of. Then begin there and start slowly and try to figure out how you might update or even just modify that a little bit within your box. Don't go out and buy seven gazillion patterned shirts because you've worn solid shirts your whole life.

That's just a waste of money and you will not actually end up wearing those. I'd say zero in on that thing and then build outward from there. That would – and don't get daunted by that process. That would be my guidance. That is very actionable advice. That's good. Thank you. Like start with the shoes, for example. Or, you know, start with something. The shoes are so hard. Yeah, but you can, most people, let's say, your weight changes as you age or your, you know, you go through surgeries or you have all kinds of physical changes.

But shoes can be one way that a person can update their look quickly, that, you know, they come in a different range of prices. you're probably not going to outgrow them. They are, you know, if you wanted to make a big investment, you could justify that because you'll wear them all the time and you'll get them repaired. Like, that's a good place to start. I feel like this is related to our next question, which is from Laura in Menlo Park, California. Laura writes that after giving birth to her son, none of her clothes felt appropriate to wear anymore.

And again, touching on this theme, we've been talking about the clothes that she accumulated in her 20s no longer matched her sense of self. She's a different person now inherently as a new parent. So she asks, quote, how do you suggest navigating this early motherhood era with regard to personal style? And how do you do so without going broke? Yeah, I would say the transition to new motherhood is one of the most profound shifts a woman is going to experience in her life, in her body, you know, in relation to others, in relation to the child. she now has to take care of. So you're also navigating a realignment to who you feel you are in the world. That's maybe the most difficult of all that I've experienced and that I've witnessed

other people experience. And similar to our other answer, I think it's got to happen gradually if you can't afford to just throw it all out and start over, which is this sort of fantasy. I don't think anybody can really, you know, unless you're a very rich celebrity chances are, You're going to have a lot of the same old stuff you always had, and you have to figure out how to make it work. But I guess not to be corny, but to be slightly gentle with yourself as you go through that, maybe pick up one or two things that you feel really good in. It's kind of the opposite of what Jacob is saying is, like, identify the thing that makes you feel the worst. But this would be like, go out and treat yourself to at least one thing that you do really feel good in, that makes – that does express that about you. Start with that.

And then wear it to death. I kind of swear it all the time. That's what I would say. Yeah, I mean, obviously I'm a man. So my answer will be very gendered in this way. But I'm a new father. My son is less than five months old as we speak. And I truly just got off leave like a week ago.

And I went through that entire period of leave dressing and almost the exact same thing every single day. I wore shorts and a old shirt, like an old tea, every day. And I did that for months, and I was fine, you know, obviously you're so sleep deprived and you're so whatever. Like, you're not seeing people. You're like, who cares? Just get me dressed like and have, you know, feed him. And I think it took until like two weeks before I came back to work, I went and I did buy something. And I bought something that was like very personal to, like, it was very like of my style, quote unquote.

a sweater. It, like, had... It's not this sweater. No, it's not this sweater. It had, like, a funky pattern to it. And it felt like I was like, oh, this is a reminder of, like, what I like and who I am. Because it is really difficult. Like, you're, like, I think I look at a lot of stuff in my drawer right now, and it feels very juvenile, which makes, like, no sense, because I only, I wore that, like, a year ago. But then there's other things where I'm like, does this make me look too much like a dad? Like, what is that? And then what does that mean? And you're just kind of tortured? by it a little bit, but I think that's a great piece of advice, Stella. All right. This one, I'm actually, I'm interested in this one as a dude who sees dudes dressing terribly. Okay, so this is from Kale in New Haven, Connecticut. Don't know where he went to college.

He is a law student who describes himself as, quote, never particularly concerned about fashion or style, but he gets anxious about making sure his outfit fits the particular setting he's in. So he asks, what are good rules of thumb I can or should be following to make sure I'm not finding myself chronically overdressed or underdress? And this touches on a theme that a lot of, I think, men asked about, which is how do they dress better than they do now without looking overly formal? I would say that what I've observed is that many men, their primary goal, I'm going to be grossly. I'm a grossly generalist is not to stand out too much. And that's, you know, there are all kinds of social reasons for that

that are above my pay grade, but, you know, are quite deep and psychological. So, you know, I don't know, you know about Red Sock theory? Do you know about that? Oh, God, please tell me about this. No, go ahead. No, you go ahead. Well, I might mingle it. But what I understand it to be is that you can pick one item.

to have a little bit of flare and that people will respond well to that tiny bit of flare but if you let's say put a red blazer on they might not respond as well you're standing out too much so you want to stand out just a little but not too much and that's what red sock theory comes from

but I do feel like maybe this person asking this question wants a little bit of flare but not too much like they want to walk a line but not why are you giving me that like because I have several pairs of red socks

That's why. Well, you're special. Oh, God. The unfortunate thing about the Red Sock theory is that a lot of people know it, so a lot of people do the same trick, so it doesn't become as memorable. I actually think I'm, like, wondering, as I sit here, I think this guy should go the other way. I mean, I feel this is like... You mean you should go formal? I think he should just wear a suit all the time.

Yeah. Well, that's a good option. Better to be overdressed. I think it's like, if I'm this guy and I'm thinking, I'm concerned to be. about being overdressed. People will very, unless you're wearing a tuxedo, they will very rarely judge you for being overdressed. I think you might feel a bit abnormal in that immediate moment,

but you're not going to be judged. And to the Red Sock theory, you will probably be remembered. And especially in this universe where I think people, men in particular, sit in this kind of weird, wishy-washy zone of business casual, sometimes too business, sometimes too casual, whatever. It's like just, I think you could lean in, wear the suit, wear a tie even.

I'd say not vary it up that much. If you're going to do that, I'd say keep it pretty, you know, standard suit, maybe solid colored knit tie, a solid colored shirt, but like get a good template going and maybe that's just what you wear all the time. And you can lean into that if you're comfortable with it.

I'd say otherwise, you know, it's tough because I think, yeah, I think too many men are in that kind of muddy middle right now where it's like, oh, here's my button-up shirt with my, like, VNex sweater over and my performance polo. And, you know, then you just look kind of pedestrian. Yeah, a lot of half-sips. Yeah, a lot of, I think the half measure, the half measure is where you're in trouble, I think. I like what you're saying, which is basically, like, be bold. Go for it.

Go for it. Why not? Can we touch on the obvious, which is, did the pandemic break the way some people think about clothing? Oh, 1,000 percent. Yeah. It's like, I wonder if she's going to disagree, but I think like. Well, it didn't change me in any way. Well, I think, okay, we got it, Stella.

I think it, I think it irreparably changed what the market for, closes. You know, I think we were maybe heading in a different direction before the pandemic. Like, you know, this is such a very specific high fashion example, but I remember being at a Louis Vuitton show just before the pandemic happened. And there were a lot of suits. And I thought, okay, this is something that people are going to try to message around. This is what the brand is going to try to package. This is what magazines might try to make editorials out of. This is going to be a talking point. And then boom, the pandemic happened. Those clothes hit the stores, but they, you know, did in a very muted way because of when they landed.

People were at home in sweatpants. I think that the casualization of everything, it's like you can't put that back in the box. You know, you can't put the toothpaste back in the tube. I think people still do, in a lot of ways, shop with how can I feel comfortable as the number one criteria? And often, I think, the only criteria. I think pulling back a little bit is like what it did to our whole society where we became disaggregated and a little siloed, that will have a profound effect on the ability for trends to kind of take hold because you can live in your little echo chamber where, you know,

boat shoes are cool and never have to confront a group of people that think they're not cool. Right. And so to the extent that the pandemic just further atomized us, yes, I think it has been profound. So this is good. This is good because Maggie from Summit, New Jersey, she has a question that relates to what you're talking about here, I think. She says she's really concerned with coming off as, quote, a trend hopper. She says that she finds that whenever she goes back to something in her closet, it inevitably feels like she's drafting off what other people are wearing, even though it's just her wardrobe.

So she writes, I feel like it's harder than ever to curate a unique personal style without parts or the whole becoming social media's latest micro trend. I guess she's worried about appearing trendy to the world, if I'm understanding this correctly. So what would either of you say to Maggie? Yeah, I think Maggie just needs to be okay with her wearing the thing. like don't worry about how people are going to perceive you in it i think also as we've discussed like everything feels like a trend all the time you know shirts are long shirts are shorts are short like pants are wide pants are narrow like everything is possible and so within that it's like

tune out that noise just if there's something in your closet you want to wear it just wear it if you want to buy the thing you're never going to be able to identify how you were incepted to buy the thing you know like you're in a store you see something that's yellow you're you're you might like it without realizing that butter yellow was the trend of last year, what have you. If you are personally compelled toward something, don't waste your time psychoanalyzing why you're compelled to it. If you like it, it makes you happy. You think you'll, you'll, you think you'll look good in it. Just wear it. Yeah, you just pulled a Miranda Priestley right there. You're like, that butter yellow that you're wearing. You may not know how it got it's the store.

I think color is still where that does, where the trickle down is still probably. the most potent. But yeah. I have a question that is going to draft off a little bit of what you're talking about here. This is Dana, Tempe, Arizona. Dana asks, quote, how can you keep up with trends while trying to limit overconsumption and make environmentally conscious style choices? You cannot.

You actually cannot. There's no ethical consumption under capitalism? Well, you can buy vintage clothing that is a choice that you can make. My personal mission would be to tell people to stop following trends in that way and to think more about what they like and to wear what they like. But I'm anti-trend. Why are you posing to be like I'm pro-trecht? I feel like you're about to argue with me.

Before you respond, what is anti-tread? What does that mean for the styles? I don't think that people should change how they look and dress and act every six months. I fundamentally think that that has been a problem with the fashion industry. I think you should not even encourage people to do that. There's something grossly consumerist and unsustainable about that behavior. You know, one thing that we haven't touched on here is the way in which trends often have to do with silhouette

and proportionality of clothing. And so, you know, the ways that something might look five years ago or ten years ago have to do with, like, how high your hemline is, how short your shirt is. You know, Jacob has a piece coming out this week about men's shirts getting shorter and shorter and shorter, not crop tops, but just sort of regular button-up shirts and how they now have a kind of a flat front.

And then I have Gen Z children who shop in thrift stores, and they sew their clothes to look like that because they can't afford brand new clothes, and it's more sustainable, and they're into that. So paying attention to the ways that designers are suggesting that you wear your clothes enables you to keep up with the trends in a variety of ways. Like you could buy an old shirt and chop it up

and make it look like the silhouette of, the quote-unquote moment, and that's a sustainable way to, quote-unquote, keep up with trends. It's also just kind of a fun, like in the sporting mode of what are people wearing. It's just one way that you can start to think about clothes. And I think the idea of silhouette, that's actually a big part of what we're talking about when we talk about trends. Yeah, I do agree with Stella. I think, you know, people want to say vintage is sustainable.

I don't really buy that 100% because I think the way vintage is treated now, it's still can treat it as, like, a very consumption-based habit. It's still more sustainable. It's certainly still more sustainable. I don't want to, like, cut into that. But, like, you know, our habit remains, like, consumption-based. Like, we still want to buy the hot new thing and feel like we're kind of taking part within fashion.

And to be truly sustainable within that is very, very, very difficult. And I also think it's worth noting that, like, you know, vintage clothes are not, you know, always better made, you know, especially now as we get closer and closer closer to things from the 2000s being considered vintage. Like, they're probably just as, you know, fast fashion disposable as a lot of stuff that's in stores. And we're kind of heading toward a weird time in the vintage market for that reason.

But, yeah, sure. But it goes back to kind of what I'm saying. It's just like, and also what you're saying, buy one thing. Buy one thing. By one thing. That's what I was going to come back to. By one thing.

That's a way that you can be more. And wear that thing all the time. Wear it a lot. wear it until you're sick of it, and you can buy your next one thing. And that instead of, you know, a lot of us grew up with this idea that, like, it's back to school, so you're going to get a new bunch of clothes, and you're going to change who you are every year. You know, I don't know if that's the series catalog of my childhood, you know, Pavlovian experience

that it's September, so I feel like I have to reinvent myself. Just went through this, you know, new pair of, you know. But actually breaking free from that idea. And, you know, I do think that the pandemic, the one way in which it really did actually change the way I dress is that I was wearing the same thing over and over and over and it felt great. And when I'd go out, I'd wear the same coat to every event. And it was fine. I didn't need a new dress. I didn't need, you know, to habituate myself to novelty. And that is actually at the answer of almost every one of these questions. It's like if you feel like you're not yourself, pick one way in which you want to alter it. If you want to be sustainable, buy less, pick one thing and wear it all the time. If you want to be fashionable like everybody else, like pick the one thing that you think is holding you back and alter that.

This is a really good advice. Our final reader question is specifically for Jacob. It is a reader named Schmilbert Shmooze from New Jersey. You also know, Jacob, should he be wearing double-pleaded trousers? All he has are flat front pants. Okay, I do think you should try double pleat and trousers. Yeah, why? So I only buy pants that have two pleats pretty much.

I think maybe these are... Now, these are one pleat today. But these are also very, very wide through the leg that I'm wearing. I think they are more comfortable. I will advocate for that. I think they are more comfortable, and I think that it is a very... The comfort aside, I think it's a very good way to add intrigue,

because it modifies one part of your outfit and everything else can remain balanced up top. Everything can remain the same. I think it makes you think a little deeper about what shoes you wear because I do have pants that seem to swallow a lower profile shoe. But I like the cleanliness of a broader pant

and how straight that line feels along the side. And I think that that looks nice. I just think it looks very sharp and you look particularly like for the workday, it's in this moment where suits are really have long faded and ties are really endangered. I think it's a way to look like clean and crisp and a little traditional

without having to really modify your entire outfit. I do know that the minute you switch, fashion will change because that's what happens, right? This is a pendulum, it is cyclical. What if I leave this booth? Right now and go by, a pair of double-pleaded trousers. That means, like, in three months from now, flat trousers, we'll be back. Okay.

Is that the laws of the universe here? Yeah, the laws of the fashion universe. We'll be right back, and when we return, we are going to end our episode as we do every week with a little game. Okay, every week we play a game And the time to play that game is now And I promise the two of you It's not going to be silly Maybe it'll be a little silly

But that's fine, let's roll with it We've talked about all kinds of fashion today But this quiz is about a piece of clothing That I think pretty much everyone has worn At some point in their lives this quiz is about jeans skinny jeans baggy jeans you love them you hate

them we talked about them they've been part of the American wardrobe for a very long time and so how the game is going to work is we have three rounds here and they're all focused on jeans in some way it's a little bit of genealogy you ready yeah oh boy

these these two cool fashion writing today is right here all right we have three rounds just are you ready tell me you're ready All right, hands-on buzzers or on laptop space bars. First round is called Behind the Jeans. I'm going to ask you a question about a notable denim moment in pop culture from the past 40 or 50 years. Once I finish reading, you can buzz in.

Please do not buzz in until I finish reading. Daisy Dukes, the incredibly short denim shorts, draw their name from Catherine Bocke. character on what 1970s television series? Bugby, which is the name I see in front of me. Stella. Was that the Dukes of Hazard? The Dukes of Hazard. Correct.

Okay. Next question. What former pop star couple showed up to the red carpet of the 2001 AMAs and matching Canadian successitos? Jacob. Justin Timberlake and Britney Spears. That is correct. Next question.

Just earlier this month. Which actress showed up to the Emmy's red carpet wearing a pair of Levi's. Jacob. Oh, from Hacks. Yeah. Megan? Megan? I don't know.

Okay. Meg Stalter. Megan Stalter. Megan Stalter. Okay. Next question. Lena, Tibby, Bridget, and Carmen are four different-sized friends who nonetheless shared the same magical pair of jeans in what 2001 novel adapted to the scripted.

in 2005. Jacob? The sisterhood of the traveling pads. That is correct. That is correct, sir. Thank you. Next question. What seminal 1957 novel about nomadic hipsters did William Burroughs once say quote, sold a trillion Levi's? Stella.

Is that on the road? On the road. Very good. You guys are both doing great. Last question in this round. Last month, Gap released an ad that has been viewed more than 30 million times. It stars What Girl Group Dancing and Gap Denham.

Jacob. Cats eye? Cats eye. Excellent. Good job. The next round is a musical round. This is a round we were calling name the jar-ist and the jong. It turns out that people do not just love wearing jeans.

They love singing about them. I'm going to play you a clip of a song that mentions jeans. You get one point if you can name the artist. You get another point if you can name the song title. These slips are quick. Be ready to buzz it. First one. Jacob.

It's Beyonce, and the song is, isn't it Levi's jeans? Levi's jeans, you're right. You got both points. All right, next. Sold my new blue jeans. Stella, Stella. It is the yard birds' house of the rising sun. It is the house of the rising sun.

Animals. The animals. The animals. I always get this. It is, yes. I was going to say. You got it. Next clip.

Jacob. It's Katie Perry in the song as Teenage Dream. Gee, you guys are, we should make this harder. All right, final clip. Jacob hit it so fast. Nellie and the song is Apple Bottom Jeans. And both of those are wrong. It's wrong.

The song is low by FloWrider. Oh, no. I totally knew that. I heard, I was, yeah, okay, there we go. All right. Final round. This is rapid fire. This is a round we are calling artistic geniuses.

I will tell you what they did. You tell me who they are. First, he starred in singing in the rain. Jacob. It's Gene-based. Yeah, Gene Kelly. Gene Kelly. Yes, great job.

Okay. You just hit buzz? You didn't even know. How you know the strategy? He's the Jeopardy guy. It's the Jeopardy guy. He was like, you buzz first. I don't know.

All right. She just won another Emmy for her role in hacks. Jacob. Is Gene Smart? Gene smart. Next, he played the title character in Willy Wonka and the Chocolate Factory. Stella. Oh, no.

Are you kidding? I let you buzz on that one. You really don't know? You do know it. You know this. It's Gene Wilder. It is Gene Wilder. I don't know how we're going to score that.

I don't know how we're going to score that one. Jacob is going to get that one. All right, this is the final question in the round and the game at large. He won an Oscar for his role in the French connection, and he also passed away this year. Jacob. Who's Gene Hackman? Gene Hackman. Stella, did you just give up over there?

Just staring at me. I just keep thinking about Gene Simmons. Why he didn't pick him? Okay. The winner of this week's quiz is Jacob. Jacob, I think we all knew Jacob had this. Right as soon as he said Nelly. Apple bottom jeans.

For some reason, that was when I hurried in my ears. I was like, oh, it's got to be Apple Bottom G's. That's coming. Jacob, I have a prize here for you. This is the fifth one of these that we are awarding. This is what we call a gilby. It is a small golden trophy with my face on it. I'm so sorry, but congratulations.

No, thank you very much. This is, I'll cherish this forever. I'm so sad not to have won a gilby. I think I only half believe you, but I think you just have to come back on and maybe we can get you one. Thank you, Jacob. Thank you, Stella, for being. on this week's episode of the Daily Sunday special. Thank you, Gilbert.

Thanks for having us. This episode was produced by Kate LaPresti, with help from Luke Vanderplug, Alex Barron, and Tina Antalini. It was edited by Wendy Doer. We had production assistance from Dahlia Haddad. The Sunday special is engineered by Sophia Landman, original music by Dan Powell,

Marion Lazzano, and Diane Wong. Special thanks to Paula Schumann. We'll be back next week. Thanks for listening.