Today, Explained - Why is personal style so hard?

Episode Date: May 4, 2025

Fashion has made a big swing from a strict set of rules to the idea that we should all just wear what we want. But personal style is still dictated by outside forces. And a lot of people don't even know where to start. This episode was produced by Victoria Chamberlin, edited by Jolie Myers, fact checked by Melissa Hirsch, engineered by Matthew Billy, and hosted by Jonquilyn Hill. Image of Clinton Kelly and Stacy London by Donna Svennevik/Disney General Entertainment Content via Getty Images. If you have a question for us, give us a call at 1-800-618-8545, or send us a note here.  Listen to Explain It to Me ad-free by becoming a Vox Member: vox.com/members.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Megan Rapinoe here. This week on A Touch More, we are launching our much anticipated book club. And we're doing it with Abby Wambach and Glennon Doyle, who will introduce their upcoming book, We Can Do Hard Things, Answers to Life's 20 Questions. Plus, we've got some fun and important updates from the W and the NWSL. And of course, we've got a new Are You a Megan or Are You a Sue? Check out the latest episode of A Touch More wherever you get your podcasts and on YouTube. Yeah, how about pants that fit?

This is a journey we're like all taking as a culture. This is Explain It To Me. I'm Jon-Glenn Hill and we recently asked you what you want to know about personal style. And man, so many of you called in to tell us. I have had a lot of trouble, I think, growing up trying to find clothes that fit me well and feel that I feel comfortable in. I'm 21. I feel like it's been a journey to figure out what I like to wear, what I feel comfortable in. It's taken me probably like three years, I don't know, throughout college. My style changed a lot. I did not know how to dress or figure out what looked good or understand

what worked for me, what I liked, and felt like it was just such a frustrating process. All this frustration makes sense. It feels like the trend cycle has gone from a season to 24 hours. Also, there were once rules for what to wear. Not anymore. We're supposed to wear what we want now. But what do you do if you don't know what you want to wear? My colleague Constance Grady tried to figure this out.

This is something that I spent most of my life not thinking about at all. I'm pretty normie when it comes to clothes. I'm just like, I will wear my jeans and a t-shirt, tell me what width the jeans are supposed to be, and I am good to go. After lockdown, once I was vaccinated and starting to get out into the world again, I felt like none of my clothes felt right for me anymore.

You know, I had all of these, like, business casual dresses and leftover skinny jeans, and I just looked at them, felt right for me anymore. You know, I had all of these like business casual dresses and leftover skinny jeans and I just looked at them and I was like, this doesn't seem quite right anymore now that I've had this year of not dressing for other people. I've changed who I am and my clothes haven't changed in a way that will keep up with that. And it was so weird to try to think about And it was so weird to try to think about getting a whole year's worth of changes done to my wardrobe in one fell swoop that I ended up feeling like maybe it was time to be more intentional and figure out what I wanted from my clothes. But when I thought about it, I had all these really contradictory desires.

You know, I wanted to look thin and also not care about looking thin. I wanted to buy really high quality things and not spend all that much money. I had a lot of desires from my clothes that realistically I didn't think could actually be met by them. You had a lot of goals. Where did you start?

Well, once I had decided that this was something I was going to try to be more intentional about, I kept poking through the personal style universe. And that's when I fell way down the David Kibbe rabbit hole. I love to help a person transform. He's this personal stylist who was very big in the 80s and kind of had a renaissance on social media. So on TikTok, there's been a trend going around of women talking about their kibbe body types.

Find your kibbe body type in two minutes. We'll start with bone structure. Let's talk about kibbe style IDs and how they relate to the costumes of Ever After. And getting into his work is like getting into astrology. Like you have to learn this really esoteric system with all these weird rules. It's all about the shapes that fabric makes when it's draped over your body and figuring out how to buy clothes that will suit those shapes best and then what kind

of style vibe that leads to, which is very fun for a certain type of personality, which includes me, but does also, I think, get a little exhausting and also leads to fixating on your body in maybe kind of weird ways. You like me are a millennial. So is it safe to assume that you grew up mainlining Stacey and Clinton on what not to wear also? And I just want to know, do you want our help? Or do you really like playing dress up?

Those jeans are ugly. Yeah, how about pants that fit? I don't know, call me crazy. But it feels like that's an option. I did watch what not to Wear religiously. I think a big part of the appeal was that it was telling you, yeah, there are very strict clothing rules. Here's what they are, and if you follow them, you'll look great.

If you don't follow them, you'll look like an idiot and we'll all make fun of you on hidden cameras. It really teaches you that there's a correct way to wear like your sensible wrap dress and your blazer and we are going to walk you through what that is. The pendulum has swung. Why has it swung so much? We went from these cinch waists and blazers to wearing business casual at the club to

... I mean, if I go into the office, there is like a dress up sweat pant that I will wear on occasion. You know, I will wear a pair of jeans. How did we change so much in the span of like a couple decades? Yeah, this is also something where you and I working in digital media is a blessing and a curse for us because I have definitely taken meetings with people who are barefoot

at our mutual office. I talked to a bunch of fashion experts about this. I was so fascinated by this question in part because Clinton and Stacey have swung the other way too, right? They're reuniting for a new show and it's called wear whatever the eff you want. I wouldn't necessarily do that show the way we did it back then. I don't think it will work. It's also not who I am as a human being. This is a journey we're like all taking as a culture.

So I talked to a bunch of fashion experts about this and I have three reasons for this swing. One that is cultural, one that is economic, and one that is more material. So culturally, over the past 10-15 years, there's been a lot more space on the internet for the movements of body positivity, body neutrality, and fat acceptance. I used to be self-conscious about my legs, but I've recently realized it's none of my business what people think I look like. You can be who you are and you can be a fat person

and you can live a full fulfilling life while being fat. Do you know what? I've just accepted I'm a big girl. All of which I think has kind of helped make space for people to think, okay, maybe the point of clothes isn't always to make me look as thin as they possibly can. You know, maybe this can be a place for more joyful self-expression that doesn't involve trying to conform to a very

specific standard of beauty. Economically, as fast fashion has taken off, the trend cycle has sped up so much that it is actually kind of impossible now to keep pace with trends the way you might have been able to 10 or 20 years before. So the idea of finding your personal style becomes really attractive in that situation because it's a way of releasing yourself from the trend cycle and from the textile waste that goes along with it. The final reason I have is more materials-based. This is one that comes from Kibbe himself,

who I cannot escape, which is that around the 1980s, we started to put a lot more elastic in clothing than we used to before. And this has fundamentally changed the way fabric looks on our bodies. So what Kipi says is that with elastic in our clothing, the silhouette stops being about the externally imposed shape of the clothes on our bodies and starts being about the way our bodies are shaping the clothes we wear. And that means that there's suddenly this huge possibility of what clothes can look like on us that has totally shifted the way that we can even let ourselves think about

fashion. Okay, Constance, you learned a lot during this whole process about the new rules or the lack of rules we have now, but did you do it? Did you figure out your personal style? I don't really know that I found my personal style. I learned a lot about the kinds of shapes and colors and fabrics that I like. I think the main thing that I figured out was what fantasy the idea of finding your

personal style is serving. For me, I think that fantasy is the idea of having some control over your individuality. Because fashion is a space where the ways in which we lack control over our lives become really clear in such an intimate way. You know, there are all these billionaires deciding what you should wear. There are all these marketers deciding how you should feel about your one human body. There are all these people who will see you every day and make their assumptions about you based on how you look. feel about your one human body. There are all these people who will see you every day and make their assumptions about you based on how you look.

So I think when we talk about finding our personal style, we're talking about this kind of dream of finding ways to steal control away from those people and back towards ourselves. ["The Last Supper"] those people and back towards ourselves. So that's Constance's fashion journey. But what about all those outside forces dictating our style choices? Who's doing that? And why are they doing it?

We'll find out after we pay a few bills. Have you ever gotten a medical bill and thought, how am I ever gonna pay for this? This week on Network and Chill, we're tackling the financial emergency that is the American healthcare system. From navigating insurance nightmares to making sure your emergency fund actually covers those emergencies, we're diving deep into the hidden healthcare costs that no one warns you about. Most hospitals in the U.S. are actually non-profits, which means they have to

have financial assistance or charity care policies. So essentially, if you make below a certain amount, the hospital legally has to waive your medical bill up to a certain percent. Listen wherever you get your podcasts or watch on youtube.com slash yourrichbff. The regular season's in the rear view and now it's time for the games that matter the most. This is Kenny Beacham and playoff basketball

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Will the East be as predictable as we think? Can the Celtics defend their title? Can Steph Curry, LeBron James, Kawhi Leonard push the young teams at the top? I'll be bringing the expertise, the passion, and the genuine opinion you need for the most exciting time of the NBA calendar. Small ball is your essential companion for the NBA postseason. Join me, Kenny Beecham, for new episodes of Small Ball throughout the playoffs. Don't miss Small Ball with Kenny Beech Beach and new episodes dropping through the playoffs,

available on YouTube and wherever you get your podcasts. Okay. How would you introduce yourself at like a party? Oh, well, I certainly wouldn't say I'm a podcaster. That's like the most embarrassing thing you could possibly say. But it is the truth. That's A the most embarrassing thing you could possibly say. But it is the truth. That's Avery Truffleman. She's a fashion writer and yes, she's also a podcaster. She hosts a show called Articles of Interest. It's about what we wear and also

why we wear it. How trends happen and who dictates them. Avery tackles all this and more on her podcast. Why we either talk about it in this really frivolous way, or we talk about it in this super bummer way that just like, oh, there are piles of clothes in the middle of the desert, piling up. And we either talk about waste and labor and the horrible historical roots of clothing manufacture,

or we talk about the frivolous superficial part of it. I really was like, oh, there's something in the middle. I think there's a way to look at clothing and look at fashion and look at our desires in the same way we look at food trends or design trends. I think it's all come from skepticism and curiosity, and then the more I learn about it, the more sort of in love with it I fall. It's endlessly fascinating. I think something that's been a big through line is trends,

you know, where they come from, how one emerges over the other. Can you tell us a little bit about that pipeline? Like, how does that happen? I mean, well, that's a secret sauce, right? Like if I knew how that worked, I wouldn't be working in podcasting, honey. No, I mean it's sort of this like all chemical process that people love to wax poetic about. Most high-end fashion brands are owned by like three companies, you know. It's either Caring or LVMH or Richemont.

It's not this like ragtag assemblage of designers kind of doing their own thing. So they're the fashion space has gotten very, very corporate and even among whatever mainstream mall brands, a lot of them have these like parent companies that are traded on the stock market that are looking to just move as many units as they possibly can. And the best way to make sure they move a lot of units is to make stuff that is, to put it indelicately, sort of boring. Like stuff that is not too weird, stuff that people will actually want to wear,

stuff that people are interested in. And there are huge livelihoods at stake. This really took off in the 80s. Designers pushed this movement called frou-frou, like mini skirts, big shoulders, sort of, like very Dallas. Mm, oh, yeah. Yeah, very like power office wear. And it was peddled out to women and they were like, no.

What? Are you kidding me? Like I go to an office, I'm not gonna wear this. I'm not gonna wear this like little mini skirt and these big padded shoulders. I need to be taken seriously at board meetings. No thanks. And so they just didn't buy. And it was this huge moment, a lot of company,

like the bottom fell out of a lot of companies. They lost a lot of sales. And so when people aren't buying, it's a death sentence. It's really, really terrible. So it was this moment where fashion companies are sort of like, well, shit, I guess we have to ask people what they want or like figure out.

We can't dictate to them what to wear. We have to figure out what they want. And it was the rise of the trend forecasting company where they could pay a service to make something of a guarantee like, okay, in two years, this is what people will want. And whether or not they obey those tips, I would say most companies consult at least a trend forecasting company because if nothing else it's a great way to hedge your bets. You know, if a unit doesn't sell you can turn to your boss and be like, well I was following what WGSN said, you know, I was like making the best most educated guess I

possibly could. Which leads us to this new sort of layer of the trend question which is like, are they actually giving us what we want or are we just buying what's there? Because if WGSN says like, this shade of green is in and that's what's in all the shops and we just buy it, are they dictating the trend to us? Yeah, that seems like such a bummer. It seems like there's this growing number of people who are refusing to keep up with trends. Does that resistance feel new? Or has that been there kind of the whole time? I mean, yeah, and it's part of the push and pull of fashion, right?

That people will say something is in and then a group of people will be like, no, I resist. And so that's the thing. It's in this dialectic. You can't you can't win. Like you're going to be if you're resisting the fashion, you're still part of the movement against it. I think it's hard to be too dogmatic. And I also think there's a bit of ignorance in saying like, I don't follow trends. It's like, come on, honey, you do a little bit.

Even in the way you wear your hair, in the way, there's just like, your skincare, whatever. There's no escape. You do, you live in your time, whatever. There's no escape. You live in your time. Yeah, there's no escape. And that's a beautiful thing. You live in your time, you live in your world, you live in your community.

You can't pretend that you're just a body in a jar not living in the world. I don't think there's anything wrong with that. But I think, yeah, this is part of the difference between shopping and fashion. I think you can observe fashion. I think you can like change the clothes you already have to be more in fashion.

You know, you can cut off your shorts. You can embroider a shirt. You can do things that make clothes keep up with fashion without shopping. And you can observe fashion and know what's in fashion without having to go out and like buy it. How do economic realities factor into the fashion industry and predictions about what's going to be new?

You know, I mean, I can't even fathom what tariff fashion is about to be. Well, I think it'll be interesting. I think a lot of companies, you know, again, because of these big institutions that have to move a lot of product, I think someone who I talked to at sort of a mid-tier mainstream fashion company was telling me that their lines are gonna have to be a lot smaller. They can't just make these huge dumps of seasons.

They have to start editing and be really specific. And I think to make one brand stand out from another, this might mean that the clothes will have to start being more signature, more interesting. That's like a best case scenario, which would be nice. Who knows, maybe they just lean into trends and basics and whatever they know will actually move product. I mean, ultimately, it's going to hurt small designers, which is the sad thing.

The most interesting creators committed to high quality are probably going to suffer, but it's going to make a huge change. It's going to be massive. Okay, so we've learned where style comes from, but now what do we do with it? How to dress yourself after the break. Tell me if this sounds interesting to you. A pickup truck, with no screens, no stereo, no paint, no automatic windows, basically no features of any kind. But it costs less than $20,000 and you get to decide almost everything about it.

That is the story of the Slate truck from a company called Slate Auto. And it might be the most interesting car we've seen in years. This week on the Vergecast, we talk all about the Slate truck, plus what's going on in the antitrust trials against Meta and Google, and why the app store on your iPhone might change forever. All that on the Verge on your iPhone might change forever. All that on the Vergecast, wherever you get podcasts. Should university presidents take public stances on political issues or remain neutral? And I think people like me who have access to platforms like yours should speak out to

stop authoritarianism. I'm Preet Bharara. And this week, Wesleyan University President Michael Rolfe joins me on my podcast, Stay Tuned with Preet, to discuss the role of college leaders in turbulent times and why he has chosen to speak out as the Trump administration takes aim at higher education. The episode is out now. Search and follow Stay Tuned with Preet wherever you get your podcasts. Does this look good on me?

And do I feel good wearing this? So we know finding our personal style is hard. A lot of it isn't even in our hands. But some of it is. That's what we went to our next two guests about, two very stylish and very online people who think about this for a living. I'm Laken Carlton. I go by the ethical stylist.

I'm a stylist with a focus on, obviously, ethics, sustainability, but also kind of unlearning all of those rules that we've kind of been indoctrinated with. And I'm Brian Sakawa, founder of He Spoke Style, all about classic style with a modern sensibility. I started in 2013 and our mission is to help guys look and feel their best every single day. Okay, so, Lagan, I want to start with you. I want to ask you about your clients. So, you're a personal stylist. Are there themes that come up when you're talking with a new client who's looking for your services?

Most of my clients have been, let's say, fast fashion-pilled. Say more about that. And they're trying to kind of unpack that. I have a lot of clients that have these huge closets full of just like the most terrible clothes that they will agree are now just terrible bought impulsively or you know chasing some trend or just all of these things that just add up to this closet full of nothing. And they want to improve their shopping habits, but also make the most of what they do have. What about you, Brian? What's the number one thing guys are asking you about?

Probably the biggest thing that people ask me is they come looking for basic advice. And along the same lines of what Laken is saying about building a sustainable wardrobe and getting rid of some things you don't need, I really believe that for guys, building a classic menswear wardrobe is one of the most sustainable practices

that they could have, because we talk about these foundational pieces. There are simple things that can be styled in many different ways, so lots of versatility. And once you get those pieces in your wardrobe, there's any number of things that you can do with them, including adding your own personal spin on things. Mm.

Laken, what's the first thing you tell someone who's like, oh my gosh, how do I figure out what to wear? Yeah, I have so many clients who just kind of default to black, you know, either it's black jeans, black shoes, black purse. I tell them to try to stop wearing black for a little bit. Just try it, you know? You mentioned, Brian, like the foundational pieces. I actually kind of push back against foundational pieces.

I don't think they look the same for everybody. Even my own foundation for my wardrobe, like I don't wear jeans, I don't wear pants. So like, what does the average capsule wardrobe advice usually look like? It's not very helpful to me, and I have a lot of clients that find that to be true for themselves as well. I'm just curious, Lake, and what do you tell them how to start developing a different type of style or experimenting with stuff? The first thing I do is if they have a lot of graphic teas, is say, OK, what other than jeans can we pair this with? And once they see, oh, that's a great idea,

then they can move into, okay, well, if I can wear it with this, then why can't I wear it with this? Just kind of giving them permission to try something else. I want to pose a question to y'all that we got from a listener. So someone sent in a voicemail and it's from a caller and it's about dressing curvy bodies. Hi, my name is Janelle. My question is, as a plus size girly, how do you know where to shop? And when you are shopping, especially online, how do your measurements play into what you

are going to buy? Like, how do you know it's going to look good on you, especially if it's online? What's the best way to go about that? Should we be taking measurements and using that to shop? Or yeah, how do you navigate that? 100%. I think it's actually wild that we have normalized online shopping

to the point that we have, and not normalized knowing our basic measurements. Because people are just guessing at it, right? And then reading reviews and it's like, okay, you've got their height and weight, but what does that mean? Where do they carry their weight? Is it in the same place as you? I think having those numbers and knowing the measurements of the things you like to wear and the shapes that you like and the shapes that you want to create. Having that in mind as you shop rather than just depending on a couple of pictures and a description, it makes a world of difference. I would also say in terms of sizing, size is just

a number. There's been a lot of people just get so wrapped up in, oh, I should be a size whatever, you know, myself included until, you know, recently. I don't care whether I'm wearing a 30 waist or a 32 or a 35. All brands are different. It doesn't matter. The first, the question you should ask yourself is, does this look good on me? And do I feel good wearing this? Don't worry about the size.

Worry about how it looks on your body and then you'll feel much better and more confident wearing that. Yeah, okay, I wanna do a rapid fire with you all. This will be really quick. Say the first word or answer that pops up in your mind. Okay, desert island piece of clothing. So the thing you can't live without.

A silk blouse. White linen shirt. Favorite brand. The Inven Firstenberg. He Spoke Style by Michael Andrews Bespoke. Wait, can I change my answer? Can you wear black with navy? Yeah.

Yes. Okay. And what is the longest you've held on to one piece of clothing? I have a blouse that I actually wore to my very first job interview. That was my grandmother's. It was huge on me then. Now it's a little too small on me now. I have had it for about 15 years.

Jared Siffman 31 years. It's a t-shirt that my band in high school made and we wore it. Kite That's not fair. I'm only 32. Jared Siffman It's a vintage item. Kite I'm curious how you all feel about how the internet has changed your relationship with fashion. Y'all are both very online. I mean, that complimentary. I am too.

Do you think the internet has made it easier or harder to figure out what your own style actually is? I think if you're still fast fashion-pilled, then it can make it a lot harder because it's very much the trends are moving, I have to keep up. But if you are already kind of in this idea of wanting to build something long-lasting and that you really love,

then it can make it easier but also overwhelming. I think the amount of content and people, different types of people, different types of styles, different platforms that speak to different demographics, I think it's fantastic because there's so much out there now and you can really find what you gravitate towards and you can find your tribe in a way, your style tribe and say, I like that, I like these people. And then what I've found, at least in menswear,

is people are generally very, very supportive. The amount of stuff available on the internet and the way we can kind of section it off for ourselves and curate it to our own tastes is a real positive. All right, thanks for explaining this to us, y'all. Thank you for listening. My pleasure. Everybody out there. Before we go, thank you for all your calls about personal style and fashion.

So we're asking for your help for another upcoming episode. Spring is the season of love and possibility, but it's also the season of allergies. ExplainItToMe wants to hear your stories of seasonal allergies, your outdoor ones and your indoor ones too, if you suffer from them. Call 1-800-618-8545 or send a voice memo to askvox at vox.com. That's 1-800-618-8545 or askvox at vox.com. This episode was produced by Victoria Chamberlain. It was edited by Jolee Myers, fact checking by Melissa Hirsch

and engineering by Matt Billy. Also special thank you to Carla Javier, who helped develop Explain It to Me and who ran our show. Carla, you have been such an amazing colleague and an incredible joy to work with. I can't wait to listen to what you make next. I'm your host, Jonquin Hill. Thanks for listening. Bye!