Episode 141: Cities and Fashion with Derek Guy, The Menswear Guy 

Doug Gordon: To be honest, it’s not easy to look stylish in the rain. But when I put on my Cleverhood Urbanaut trench, I get that perfect balance of stylish design and excellent functionality. Not only does it look great, but it has reflective details that shine brightly in the dark, and quality craftsmanship and attention to detail that keeps me dry when I’m out and about. There’s also the Rover rain cape. With its striking colors, it always turns heads and it fits comfortably over whatever I’m wearing, so when I do show up, I don’t look like a hot, wet mess. Listeners of The War on Cars can save 15 percent on everything in the Cleverhood store. Just go to Cleverhood.com/waroncars and enter code RAINSTYLE at checkout. Again, that’s Cleverhood.com/waroncars, discount code RAINSTYLE. Stay dry and look good with Cleverhood.

Doug: This is The War on Cars. I am Doug Gordon, and I’m sitting here with my co-host, Sarah Goodyear.

Sarah Goodyear: Hello there.

Doug: How’s it going?

Sarah: I’m good. I’m actually feeling pretty good today.

Doug: That’s great. I want to talk about fashion.

Sarah: Okay.

Doug: I am not a particularly fashionable person.

Sarah: Mm-hmm.

Doug: I guess I clean up well. I don’t think that means I don’t think about fashion. I’ve got a real work-from-home aesthetic going on these days, as I think a lot of people do. How about you? I always think you’re pretty fashionable.

Sarah: Thank you, because I like to think of myself as somewhat fashionable. I like getting dressed. I like thinking about what I’m gonna put on. I like clothes. I like different styles. I like being able to be playful. Yeah, I do think about what I put on in the morning pretty carefully.

Doug: My daughter said to me—because we’re gonna be going out on a book tour in a year. She said, “Papa, you gotta step it up.” She said she wants me to get a really nice pair of jeans, Air Jordans, and some sort of dark-colored shirt. I’m like, “Okay, I’ll do that.” So she’s gonna help me shop.

Sarah: Okay, that sounds like a fun father-daughter expedition.

Doug: Not bad.

Sarah: Yeah.

Doug: Okay. Well, we have a guest who is gonna help us talk about some of these things. It should be a really fun conversation. Before we get started …

Sarah: You can support us on Patreon. Go to Patreon.com/thewaroncarspod, and sign up for as little as $3 a month. You get bonus episodes. You get early access to live show ticket sales. You get all sorts of goodies. You get a signed note from usually me, and you get the good feeling that comes with supporting The War on Cars.

Doug: And speaking of live shows and presales, we are gonna be in Minneapolis for a live show. That’s on Thursday, April 24 at the Cedar Cultural Center. We are being brought out there by Our Streets, which is an awesome local advocacy group working towards equitable transportation and urban highway removal. So presale tickets are available for that show if you’re a Patreon supporter. We’ll put a link in the show notes. Also, if you are a sustaining donor of Our Streets, you can get tickets in advance. If you live in the Twin Cities, you really should be supporting Our Streets. They’re doing awesome stuff with highway removal, advocating for people first infrastructure that isn’t centered around cars. We love these people. They’re really great. We cannot wait to get out to the Twin Cities. So act fast because that presale is open now, and then it opens to the general public on January 12.

Doug: On to the main event. If you think of the fashion centers of the world, you probably think of New York, Paris, Milan, Tokyo—which we’re gonna get to. I’m sure people could name a lot more. And just about all of them are places where when it comes to fashion, people tend to put their best foot forward—literally. So how does walkable urbanism, density and safe streets influence the way in which people dress? Our guest has some theories. You may know him as The Menswear Guy on the platform formerly known as Twitter. He’s now on Bluesky and other social media sites. His writing has appeared in the New York Times, the Washington Post, Esquire, the Financial Times, Put This On and a lot more. You can also find his thoughts on men’s fashion on his website, Die, Workwear. Derek Guy, welcome to The War on Cars.

Derek Guy: Thank you so much for having me on. It’s really fun to be on your show.

Doug: I think a lot of our listeners probably know who you are because you had this really unlikely rise to fame. Let’s talk a little bit about Twitter, and I guess we’ll call him “He Who Shall Not Be Named.” When he took over the platform, your account started showing up in the “For You” tab, and just was kind of thrust into a lot of people’s feeds. And you very quickly amassed tons and tons of followers who are following you for your fashion writing and your observations on a lot of elected officials and what they were wearing, celebrities and what they were wearing. But where you really came to our attention were your thoughts on walkable urbanism and cities and things like that.

Derek Guy: Yeah. Sometimes people—I mean, I do deviate a little bit. I try—as my account has grown, I’ve tried to keep it focused on menswear, but I do sometimes deviate a little bit. And I think sometimes the walkable neighborhood part is a little bit odd to people. I do kind of, I admit, shoehorn it a little bit in by trying to tie it to clothes, but I do think that walkability and urban design is related to clothes in some way, in both how designers draw their inspirations and, you know, the kind of cultural—the culture that comes out of urbanism, and also our motivations to whether or not you’re actually even motivated to, you know, wear a nice outfit and go out. I mean, clearly, to be clear, I don’t think fashion is the most important reason why we need walkable neighborhoods and affordable housing and all that, but since I do mainly talk about men’s clothing, then I try to tie it to men’s clothing to some degree.

Doug: Derek, I know you’re very private about your personal life, but I was wondering if you could tell us a little bit about your own personal relationship with cities and driving, and how you became interested in this topic that you say you sort of shoehorn into your other obsession.

Derek Guy: Well, I admit part of it is—I don’t think my experience is that different from a lot of people, whether they live in a walkable neighborhood or not. I have seen a larger and larger percentage of my income over the decades get eaten up by rent. I don’t own my own home. I’m a renter. And I have a strong preference for walkable neighborhoods. I didn’t really think about that until relatively recently. I remember when I was young, I was driving. I picked up a college professor from the airport to drive them to a talk. And this professor was, I think at the time, in his, like, maybe 60s or so, and he had mentioned that he had not owned a car, like, almost ever. And I thought that was so strange. I was like, “How do you get by without a car? That’s such a weird—” I didn’t press him on it. I just thought that was strange.

Derek Guy: But now I have not owned a car in decades. And it’s—you know, when I think back of all the places that I’ve lived—San Francisco, New York City, Moscow, other places—I’ve made a conscious decision to live in walkable neighborhoods just because I just think they’re more enjoyable. And the price has gone up wildly, and I would just personally like to see more walkable neighborhoods so that I have more places to choose from in terms of living, and don’t have to pay, you know, like 50 percent or plus of my income in rent. That’s really the core motivation is not wanting to pay so much money in rent.

Sarah: This is one of my pet peeves. Walkable neighborhoods have now become a luxury good. In the United States of America, you cannot rent an apartment in a walkable neighborhood for the most part unless you’re affluent. And how that happened is a very sad story. And obviously there are a lot of factors, but it kind of dovetails with this whole idea that is completely fallacious, which is that being in favor of walkable neighborhoods makes you an elitist. That has now become collapsed, that because you have to be rich to live in a walkable neighborhood now, the perception in the culture war conversation is that you’re an elitist if you like walkable neighborhoods. And it should just be the default. And indeed, of course, in much of Europe and Asia it is the default. But in the US, yeah, there’s just this vanishingly small number of places where you can live a truly car-free lifestyle and feel completely enfranchised as a citizen of that place.

Derek Guy: Yeah.

Sarah: And it will cost you a ton of money.

Derek Guy: Yeah. I remember years ago I got kicked out of my apartment because I was living in a place and someone, a couple, bought my building and decided to move into my unit. So I then had to, you know, vacate the unit. So I had to go look for a new apartment. And I remember going all around to different walkable neighborhoods and trying to, you know, find a place that I could live in. And one was very—I mean, they were all bad. [laughs] The spots that I saw were so bad.

Derek Guy: One was particularly bad. It was, like, in the basement, like barely any sunlight. And I remember there was a line outside, and in the line to see this unit was an elderly woman, and then two guys that looked like they were going to share the unit, like they were laborers that were going to split the rent in this very small unit. And I was just thinking, like, I don’t—I don’t want to compete with—like, I don’t want to be the reason why an elderly woman is not able to live in this unit. Like, this is a bad situation.

Derek Guy: You know, anytime you go to kind of any rental showing in a walkable neighborhood—I think that’s still common even in 2024—there’s always a line. And you see all sorts of demographics out there, and you just think, like, “Man, it’s just not a good situation for all of these people to be competing for the same unit.” So someone recently asked me, someone interviewed me for some blog and asked me why do I like walkable neighborhoods? And I kind of think it’s almost like a visceral sensation. There are some people who prefer to live out in rural areas or suburbs, and I think that’s fine. Like, if you—if you want to live in a different, you know, kind of lifestyle, I think that’s fine. But to me, a walkable neighborhood is almost visceral. Like, I enjoy only having to go walk 10 minutes to get groceries. I don’t want to have to drive very far to go get groceries. I like to be able to walk around, like, some trees and a nice neighborhood. I like to be able to do everything that I need without having to pay, you know, like $500 a month for a car. I like to not have to worry whether or not someone’s gonna, like, bump into my car and have to pay to repair it. I don’t have to think about all that stuff. I just want to be able to walk and get my stuff, go to the, you know, whatever, the dry cleaner and the grocery store and the post office, and have that also be a break from life at home. To me, that’s like a very visceral, basic enjoyment, and happens to be something that everyone else apparently also likes, which is why these units are so expensive.

Sarah: Yeah. But somehow it’s also in our culture considered kind of weird or subversive to put so much emphasis on wanting to be able to walk to things instead of driving. You know, driving is normal, and walking, even though it is something that’s desired by so many people, somehow has become not normal. It’s very strange.

Derek Guy: I remember I wrote once on Twitter that I like being able to go to the grocery store and just pick up enough ingredients for my dinner. And I do that pretty often, and I treat my local grocery stores like my fridge. And someone said, like, “How is that enjoyable? Like, you have to go out all the time to buy groceries?” And obviously you don’t have to. You can go out and buy, like, you know, two weeks worth of groceries, but I take it as just a bit of exercise. Whereas I wouldn’t like it if I had to go all the time, drive 20 minutes or something to a grocery store and figure out what I’m gonna eat for the next two weeks and then, like, plan accordingly. Whereas now, like, if I decide I want tacos tonight, then I can just go to the grocery store, it’s a 10-minute walk, and then grab my ingredients for tacos and have, like, the freshest possible cilantro and not have it be sitting in my fridge for forever.

Doug: Sarah was saying, you know, if you’re focused on these things, if you live in a walkable city, there’s a sort of air of elitism that is pushed onto you. You know, we advocate for these things, and sometimes we are told, “Oh, you’re an elitist who has all this time to get around by bicycle.” Or whatever it is. I think an obsession with fashion can sometimes be seen as that as well. Although Derek, your interest in fashion often is kind of similar to the affordable housing angle in that you’re looking for well-made but inexpensive items of clothing that are of a quality—I think you can sort of relate this to, like, good old cities and what used to make them great places for all people to live. Am I shoehorning too much here? Am I trying to make that, you know, the square peg-round hole, or is there a similarity?

Derek Guy: I think of clothing as just a hobby for me. So I think it’s fine if other people don’t share my hobby. I think it’s totally reasonable and fine. There are lots of things that I’m not interested in. But if you—getting dressed is one of those things that, like, we all have to do if we go out in public. So I just think that if you have to get dressed, then it’s nice to be able to put on clothes that make you feel good versus make you feel bad or indifferent. And that can be done at any price point.

Derek Guy: And I do think that there is a bit more motivation to do it if you live in some kind of walkable area. I remember when the 2020 lockdown happened, somebody tweeted something really funny. They said something like, “I’ve just realized that I don’t actually dress for myself.” [laughs] And I think, you know, like every—that’s like a common refrain, right? Like, people say, “Oh, well, I dress for myself.” But it turns out that actually if you don’t go out and no one sees you then, you know, like, you might put on clothes that you find comfy and you like, but you don’t necessarily put in the effort for, like, the full presentation.

Derek Guy: So there is something about the act of getting dressed that’s not necessarily about impressing people, but it is—somewhat requires some kind of audience. And I think that motivation is diminished if you live in home, get into a box that is your car, transport yourself in a fairly private kind of container, and then move yourself into a building where then you work in a cubicle for however long, and then you get back into your box on wheels and you go back home. I think the motivation is a little bit diminished. Whereas if you—certainly if you walk around a neighborhood, if you get on public transportation, I think there is something. There is some extra motivation to look, you know, however you want to look, whatever that expression may be. And I think that just makes things a little bit more enjoyable.

Sarah: We also tend to think that the choices people make about transportation and fashion are sort of arbitrary sometimes, or just, you know, consumer preference or whatever. But there are these massive industries behind clothing and transportation that are influencing our behavior. I’m curious. I mean, in our side of things, we see this constant barrage of advertisements about cars, and what kind of cars and bigger and bigger SUVs that you’re supposed to be driving, and that’s what’s being normalized by the advertising environment. I’m interested to know when it comes to clothing, what messages you think people are getting about what they should be wearing, and are those good messages, bad messages? How are they affecting the way we feel about what we put on our bodies?

Derek Guy: Hmm. I think that a lot of fashion advertising falls flat for many people because a lot of fashion advertising is like, “This celebrity wore this thing,” or “This is like the trendy item.” I don’t think that actually resonates with very many people. And I actually don’t really care that much about that kind of advertising. I think of dress as social language, so I think that people tend to dress to signal that they’re part of a group, but also an individual within the group. And I think that’s true even among people who say they don’t care about clothes. They tend to dress in a way that fits in with their specific crowd. And that can be a kind of socioeconomic crowd, that can be gender identity or sexuality identity. It can be an identity to—you know, if you’re dressing for work, you might dress in a way to say—to communicate that you’re professional or whatever.

Derek Guy: And I think those are the cues that most people orient their shopping purchases. I don’t think that most people really care that much about fashion advertising, same way as I don’t really care about fashion advertising. But it is harder for consumers now to figure out where to buy those clothes because there are just so many options on the market. I just don’t think that the industry has a very good handle on marketing those things to you, partly because it’s very hard now for brands to reach consumers in a way that I think is meaningfully driving their purchases.

Sarah: I grew up in New York City. I grew up in Manhattan. And my whole life, one of my favorite things has been to see if I can sort of spot what the next trend is gonna be, to watch the people on the subway. And it’s true, you’ll see somebody wearing something. For some reason, I’m thinking of Kangol hats back in the ’80s. And it’s like, “Wow, that’s a cool hat.” And then you turn around, and all of a sudden the next time you’re on the train, there’s 10 people wearing that hat. And then all of a sudden every vendor on the street has them and is selling them. And oh my God, I can get one of those. And this knockoff one is only five bucks or whatever. And you see it happen. And so, like, in a way, that’s how we advertise fashion to each other, right, in New York is on the train and you just, like, admire somebody else’s look and you try it on for yourself later. And I just love watching that phenomenon, which is a really, truly urban phenomenon, I think.

Derek Guy: Yeah. One of the things that I lament, at least in my corner of the world, is that there has been—the skyrocketing rents means that there has been a huge demographic shift in San Francisco. So whereas there used to be more diversity, both in ethnic diversity and more importantly class diversity, it has become a little bit more homogenous. A friend of mine puts it as San Francisco is a town for people from all rich walks of life. And I think of that in the sense that I think that’s detrimental. Again, this is—ranks very low on the list of, you know, cultural and political and economic priorities. But if we’re to link it back to fashion, I think that is detrimental to fashion in the sense that designers are often drawing inspiration from the kind of various subcultures that exist within cities. So they draw, you know, inspiration from youth subcultures, underground subcultures, punk, skate, the way musicians and artists dress, the way, like, you know, like crunchy, kind of like outdoors-y types people dress.

Derek Guy: And when you start to see that a city is filled with people who consume those aesthetics, but are essentially all coming from the same socio-economic, sometimes even racial backgrounds, I think you’re suffocating the language that the well of inspiration that designers can draw from. When they’re walking around the city and all they see are middle- to upper-middle-class people who shop at, like, you know, cheese shops and, you know, fancy bread stores, you end up recycling the same design languages over and over again. You don’t have that kind of, like, diversity in culture that allows a designer to say, “Oh, wow. That’s a really interesting thing that’s happening at the moment, and it’s being worn in a way that communicates a kind of cultural cool. And now let me do a riff on the Kangol hat or tracksuits or the way people are wearing gold chains or the way people are wearing baggy pants or whatever, you know, the aesthetic is.” A lot of that relies on a kind of vibrancy in street culture, which is—I wouldn’t say it’s dead, but it does feel very different than where it was 30 years ago, when rent was more affordable.

Doug: We talk a lot in urbanism circles about “indicator species.” If you see a kid cycling by themselves to school, you know, a mom cycling with kids, an older person cycling alone, that’s a good indication that your city’s doing something right with its streets. You know, I think you could probably say the same along the lines of what you’re talking about, about small storefronts and artisans and things like that. You know, one of the problems I think a lot of cities are having is as they try to catch up on the housing front, the stuff that is getting built does not enable ground floor retail at the size and scale you need to craft a culture of artisans, of tailors, of any sort of creative profession. Instead, you get really big commercial storefronts that only then allow for a medical office, a drugstore like a Walgreens, a chain drugstore, or large corporate clothing stores. I think you had a post about J. Crew or something like that replacing your smaller little tailors or little bespoke shops. And that has an effect, too.

Derek Guy: Yeah, I remember there was a project—I’m always on the lookout for, you know, whether there’s a walkable development being, you know, kind of done somewhere local to me because I want to check out the housing prices over there. So I remember years ago they started this walkable kind of living community near a BART station. And I was like, “Oh, that’s gonna be really interesting. Like, I wonder how much the units are gonna be, because if it’s—if it’s gonna be a significant savings, then maybe I’ll look into it about moving there.” And I remember when it opened, I went there and took a look, and it was walkable in the sense that, you know, the distance between your living unit and some commercial space was relatively collapsed. But then you go, and the commercial enterprises are like Panda Express. And, you know, it’s no knock on Panda Express. Like, you know, I think it’s fine if you enjoy eating there and whatnot but, like, if all of the stores are Panda Express and, like, I want to be in a walkable neighborhood that’s just not a bunch of chain stores.

Derek Guy: And it may be that sometimes some, you know, restaurant might not be as good as Panda Express, but I appreciate the little bit of diversity in the experience. And I also think that those kind of—when you build smaller units that, you know, some guy who’s passionate about ramen or whatever, they can, like, set up a stand somewhere, it allows those kind of hobbyists to create a business. I was talking to a friend the other day about how I think the shopping experience for almost anything now is just totally absurd. You essentially—there are so many options on the market that you have to do all of this research and, like, figure out who’s basically a shill or not a shill and, like, who’s providing good information and who’s an expert. It’s just—it’s just absurd to buy anything nowadays.

Derek Guy: But what it should be is that you should be able to walk to a local store that’s run by some nut who is passionate about that thing; that’s like all they care about. And then you should tell them what you need, and they should tell you what you should buy. You know, let’s say if I wanted to buy a bicycle. I don’t know anything about bicycles. And I don’t—I don’t feel that I should have to research and look on forums and figure out who’s, like, the more informed posters on that forum and do all this research and read blogs and reviews and stuff. I should be able to go to a local bike store whose run by that kind of, like, bike nut and then tell them, “Well, I need a bike to do—this is my lifestyle, this is what I do on a daily basis. I need a bike to do these things.” And they should be able to tell me what bike I should purchase. But at the moment, a lot of times you go to a bike retailer and if it’s run by a chain, I just don’t think you get the same kind of passionate service. I think a lot of those people are then just doing it for their job and they’re happy to make a commission, whereas I think if you get more hobbyists in that kind of commercial setting, they take a—I don’t want to say more pride in their work, but I do think that they will hopefully make better recommendations.

Sarah: I was thinking about I was in Bologna, Italy a couple of years ago, where I have some family. And near the university, as in much of the city, there are, you know, these very ancient buildings, medieval in many cases, and there are these incredible colonnades that cover just kilometers and kilometers and kilometers of the sidewalks of Bologna. So in any weather, whether it’s hot and sunny or raining or whatever, you can stroll along these colonnades, and there are all these tiny little storefronts in the buildings. And as I walked along, you know, you’d look in, there was a person who was obviously a fashion designer with their sewing machine making something brand new. There was a vintage shop where I went in and I bought way too much stuff because the woman, as you say, was so passionate and knew exactly as soon as she saw my taste, she was able to bring other things off the rack for me. There was a bicycle store where a guy who clearly could fix any kind of bicycle and cared so much about bicycles was sitting there. And that sort of lovely village feeling of all the weird obsessives who have their things that they are obsessed and knowledgeable about then share that with other people and make it available to other people—their expertise as well as the actual material goods. And that is a kind of commerce that is not as sterile and boring as the kind of commerce that we have now.

Doug: It’s also, I think, you know, we have a sort of Main Street USA feeling in our neighborhood here because we do have the places. Like, I can name three places to get shoes repaired within a 10- or 15-minute walk or five-minute walk of my apartment. There’s not just a hardware store, but there’s a little storefront where they just make keys and repair watches. Those are the kind of things you don’t see as much in strip malls or, you know, more new suburb kind of developments. And I think that has an influence on fashion, of course. I remember when I was in my 20s, I bought probably the most expensive pair of shoes I’ve ever purchased before or since, this pair of boots. They cost, like, $275, which at the time was a large portion of what I made in a week. And I rationalized it because I said, “Okay, they’re gonna last forever because I can get them fixed. Hopefully I can get them fixed for the rest of my life.” I still have those shoes, like, 25 years later, and just had them spruced up last year. So I think there’s something also to be said about disposability and what a suburban culture does to consumer preferences including, of course, fast fashion and style.

Derek Guy: Yeah. I think about a friend of mine, Seiji McCarthy. He was born in the US but moved to Tokyo, I think maybe about 20 years ago or so now. He moved to Tokyo to learn bespoke shoemaking under this other Japanese bespoke shoemaker. Now he runs his own operation, just operating under his own name, Seiji McCarthy. And I remember when he visited San Francisco, I did a podcast with him, and I asked him why is Tokyo so much more interesting in terms of fashion? And he hypothesized—well, I should explain. Tokyo has more bespoke tailors and bespoke shoemakers than you’ll find across the entirety of the United States. So it’s not to say that everyone in Tokyo is getting a bespoke suit, but if you wanted to get a bespoke suit or bespoke pair of shoes, I mean, you just have, like, tons of options. Whereas in the US if you’re outside of New York City, there aren’t that many options. And if you are in New York City, you’re mostly relying on traveling operations: people, tailors and shoemakers that live in other countries, and then come through the city every once in a while and take orders and, you know, conduct fittings.

Derek Guy: And I asked him why are there so many bespoke tailors and shoemakers in Tokyo? And he said that he thinks it has to do with the cost of living, and primarily rent. He estimated that the cost of living in Tokyo is a third of what it would be in New York City or San Francisco for a comparable kind of lifestyle. And he said the ability to get a very small commercial space and to do it cheaply and affordably allows someone to pursue their passion. So he says—he talks about how, you know, in these kind of, like, walkable communities, you can walk for a while, and then you’ll see a guy has a bar and there’s only, like, three stools, and you wonder—or he has a ramen stand with only three stools, and you wonder, like, how can that person run a business that only serves three people a time? And it’s because the rent is really low and the space is very small. So that person who’s passionate about whatever, beer or ramen, can afford to pursue their passion and only serve three people at a time. And similarly, for him, I don’t know his output numbers, but most independent shoemakers that I know put out maybe between 10 and—say, like, 10 and 40 pairs of shoes per year. So I would estimate he’s probably somewhere in that range. And, you know, like, that’s not a huge output, but it’s enough to pay rent for both his commercial space and his private living space. Whereas if you have a really large store, you know, you have to sell, like Foot Locker kind of numbers.

Doug: There’s also the walkability angle in that they get a lot of foot traffic in places like Tokyo or New York City. So a small shop, even if it just has three stools, if it’s turning over those three stools dozens and dozens of times per hour …

Derek Guy: Right.

Doug: … then it can do all right. Whereas if you were to open a very small 10-table restaurant in a strip mall, you’d have to do a lot of advertising to attract people. It has to be a destination. You’re not gonna get people just driving by and saying, “Let’s stop.” I think a lot about the Jane Jacobs quote, “New ideas need old buildings,” and how we’ve designed so many of our newer cities that the new buildings can’t really be anything other than what they were always intended to be.

Derek Guy: Yeah. And ultimately at the end, the consumer is paying that advertising cost. The brand is not eating that entire cost, they’re passing some of that cost to you. So you end up paying more money for not an improvement in quality. I mean, that’s also a bit of a catch is I think if you do live in these neighborhoods, you have to patronize some of these shops. I would hope that people don’t just, like, go into the shops and then, like, you know, try on the sizing and buy it online. Which does happen, but I hope that, like, in order to get the—in order to support these businesses, you have to sometimes, like, shop local. You have to throw some dollars to the stores that you think bring value, even if it’s just the value of their storefront on your walk.

Sarah: Yeah, I think that something along those lines actually happened in Brooklyn during the pandemic because people are so hyper aware of the value of these businesses to sort of maintain the nature of the neighborhood. People got together on social media and were talking about, “Oh, you know, buy this here, buy that there.” And you really saw people consciously shopping in order to save their businesses that make their neighborhoods what they are. But you made another interesting point—I saw it on Bluesky—about Tokyo, that’s like next level to me, which is you talk about the fashion press in Tokyo and Japan and how granular it is, and how there’s so many publications, especially about men’s style, that get into these incredibly arcane details of dress. And that ecosystem for their distribution is newsstands that also depend heavily on being in walkable neighborhoods.

Derek Guy: Yeah, someone had tweeted something about “I’m in Japan right now, and any aesthetic that you can think of, the Japanese do it really well.” So it could be classic tailoring, it could be minimalism, it could be avant garde streetwear. Whatever it is, they do it really well. And under that, there are a bunch of people who gave theories on why that may be. I tweeted my take, and I think many times when people talk about Western and Eastern, quote-unquote “differences,” they often get into cultural differences. Like, “Oh, like, Asians are so, you know, observant of traditions and, like, so honorable or whatever.” I’m speaking as an Asian person.

Sarah: [laughs] Right.

Derek Guy: And I do think—I do think that culture matters. I don’t discount culture. I think there is some element of how culture can shape behaviors and outcome. However, I do think that sometimes the explanatory power of culture shrinks as you dig deeper into a subject, and you find out sometimes there are—there’s, like, historical path dependency. There may be political institutions, there may be economic reasons, there may be geographical reasons, whatever. There are often some other kind of explanatory variables that help explain the outcome. And some of those explanatory variables can also determine culture, which then culture is a secondary variable to explain the outcome.

Derek Guy: So I was saying that specifically in this context of what I would call the hobbyist, the fashion hobbyist, of which I would consider myself one, it is true that in Japan, there are a lot of hobbyists. So there are guys that are, like, super into 1960s Brooks Brothers sack tailoring. And there are some people who are really into goth-y streetwear and raw denim. They—you know, there’s a whole community of people in Japan that are, like, really into different types of denim, how they’re woven, the finishing, so on and so forth. And the question is: why is it that there are so many of these hobbyists? And I remember on a menswear forum one time, this issue came up, and people once again came up with this idea that, “Oh, well, you know, the Japanese are just, like, very, you know, observant of details, and they’re very detail oriented and they’re very smart.” And I—you know, I don’t know. [laughs] It’s like sometimes some of those things are, like—you know, I made a joke on Twitter, like sometimes, you know, I’m a little bit put off by the kind of like, racial reductionism. But then I’m thinking, like, “Wait, do people think the Asian people are better? Does this benefit me somehow?”

Sarah: [laughs]

Doug: [laughs]

Derek Guy: You know, maybe I should—maybe I should let this one slide. But I don’t think that it’s really about that. I think that what’s happened in Japan is that there’s an incredible market for hobbyist publications. So there’s a Japanese bookstore in San Francisco that anyone can go to. I can’t remember the name. It’s like Kinyono, something like that.

Sarah: Kinokuniya.

Derek Guy: Yeah, there we go. Look in Japantown and in the mall. And if you go there, you go to this bookstore, and they carry only a fraction of the kind of hobbyist publications that you’ll find in Tokyo. But you can find some of them in this bookstore. And you’ll find that there are Japanese hobbyist publications for whatever, like, whiskey and woodworking. And there’s—in menswear, there are magazines dedicated to just classic shoes—not even sneakers, of which there are also publications—but just classic leather shoes. There are publications just for work boots. There are publications for just jeans.

Derek Guy: And the weird thing to me is that these are periodicals, meaning that these people that run these publications are, like, publishing multiple issues on this very niche subject, which to me is like, don’t you eventually run out of things to say? But apparently not.

Sarah: [laughs]

Derek Guy: But the thing is is when you open these publications, they’ll have, like, a spread of 50 different mid-century chinos, and all the different ways that they differ, and what is a twill versus a plain weave. And they’ll get into all these details. And I think that the availability of these kind of publications allows for this kind of hobby. So you imagine if you’re a worker in Tokyo. You get off work, you live in a walkable city, you’re walking to the subway, and along the way you hit a newsstand, and you pick up, let’s say, hypothetically, a publication on denim that you’re gonna read on the train. You buy this publication and you get on the train, you read it, and you learn about all of these specialty denim things. And you go back to that newsstand, you might pick up one on—you know, like a workwear publication. And if you buy enough of these publications, you become interested in all of these terms and these specialty cuts and the historical kind of—you know, the stories behind, you know, the Levi’s 1947 501 or whatever. Then that motivates you to go out and go to some of these specialty shops and buy this kind of item.

Derek Guy: And I think that’s how you have the growth of all of these hobbyists, both communities, these consumers. The Japanese consumer who has read all of these things tends to be more informed in a hobbyist way than your average American consumer or even the average Japanese consumer that may not care about denim. That informed consumer is then the baseline for the support for these specialty shops. And to me, that whole system, that ecosystem, the affordability to make a print publication around a niche hobby, and then to distribute it through these newsstands to reach consumers who happen to be walking by, and then to have small storefronts that sell these niche items is basically what allows that one American tourist who was in Japan and saw all of the stuff and then tweeted, “Wow, like, these people do all these aesthetics really well.” And it’s not necessarily because the Japanese are reverent or more detail oriented or whatever. It may be—you know, I have no opinion on those cultural differences, but to me, a better explanatory variable is the presence of hobbyist publications getting into the hands of people who can then go to small storefronts and engage in these hobbies. And that is, to me, more of a walkability and urban planning story than it is about the supposed innate kind of qualities of Asian people.

Doug: And not just walkability, because there’s, I think, a really important part of that ecosystem that you mentioned, which is the time to read that publication on a commute on a train.

Derek Guy: Yes. Yes.

Doug: You know, when I stopped commuting to work, I stopped reading my New Yorker magazines or books in general, because I lost the 20 to 40 minutes, depending on where my jobs were located, of just downtime, no internet. So I think that’s really interesting. You know, and here in the US the only place you really find newsstands anymore, outside of a few big cities, are airports. And what do you see there? Road & Track, Car and Driver, Guns & Ammo, financial publications. You do see fashion publications, Vogue and things like that.

Derek Guy: Yeah.

Doug: But I think that says a lot about our ecosystem here in the United States, and how we interact with transportation and culture.

Derek Guy: Yeah, on the menswear side—I don’t know anything about women’s wear, but on the menswear side, when you go to those airports and you find those publications, those are not hobbyist publications. Those are really large publications that tell you one, if you buy one of those publications, let’s say, you know, like, 90—maybe not 90 percent but, like, over 50 percent certainly of the publication is not even about clothes. It’s about, like, latest movies and celebrities and sports and whatever. There’s a lot of stuff packed in there that’s not about clothes. And then to the stuff that is about clothes, even as someone who writes for a lot of those publications—trying to say this without getting fired. [laughs] But, you know, it’s like it’s focused on, like, what a celebrity wore. It might be a feature on a brand, but it’s like it feels very marketing PR. I don’t feel that I’m being ungenerous. I think if anyone picked up one of these large American or Western European publications and they compared it to a Japanese magazine, they would see the difference.

Doug: You mentioned that you’re not—you are the menswear guy. You don’t write or talk that much about women’s fashion, but we know fashion is incredibly gendered. But so is transportation. We talk about it on the podcast all the time. I wonder if we could talk about those overlaps between how men think about fashion and how they think about how they get around and how they present themselves to the world. I was thinking a little bit, you know, when it comes to transportation, men—I’m being very broad here, but I think men like to think of themselves as focusing on the technical aspects of transportation. But there’s lots of research and just the way car ads work to show that that’s probably not so true. It’s about presenting themselves to the world and how what they drive says about them. I’m thinking a lot about my time in Los Angeles when I was just getting started in television. I remember in my early 20s going out to see people, and they would live in just these absolute shithole apartments and then drive the nicest car possible because that was how they presented themselves to the world, and it was the first thing anybody noticed about them. What are your thoughts on sort of like gender and transportation and transportation as a fashion choice?

Derek Guy: Yeah, I remember 20 years ago there was this narrative of men—like, women shopped according to trends and impulse, and men were these, like, rational buyers and they, like, did all this research and bought things according to the technical specs and quality and all of that. I do think that men do—really, like, do a ton of absurd amount of research into, like, pants and shoes and talk about the build quality. I think for clothing, my theory has always been that men are very anxious about the act of self fashioning. So I often think that they are buying according to these, like, specs, partly because they want to feel better about the act of self fashioning. And oftentimes they’re buying something just for the same reasons anyone else is: to look cool, to look good, to feel good. And oftentimes the best way to shop is to actually just admit that and hone in on that, and figure out whether you look good and feel good in a piece of clothing. You don’t have to do all this, like, technical breakdown. But certainly, I think that is probably also true of cars, and I think that’s true of a lot of things.

Derek Guy: A friend of mine—again an American but now living in Tokyo, his name is David Marx, M-A-R-X, same as Karl Marx. And he wrote a book called Status and Culture, which is about how our pursuit of status shapes culture. And it’s kind of, for the purpose of driving, an argument to say that essentially almost everything in culture can be explained by people’s pursuit of status within their group, and then also within the kind of broader context of social hierarchies. And yeah, I assume as someone who doesn’t know anything about cars, I assume that a lot of people buy cars partly, you know, as status items to demonstrate something about identity. Eddie Bauer did a collaboration in the ’90s with a car company, I think maybe Land Rover or something. And I think it was pretty clear that none of the people buying this car were going to do any of the off-roading and all of that kind of stuff. But it was sold on the premise that you were a kind of rugged individual, and that this would signal something to your peers if you bought it, that you were, you know, like a rugged man and was connected to the outdoors and had these—like, supposedly these skills to—these survivalist skills. But most of all, it was a fashion item.

Doug: It was the Ford Explorer, by the way.

Derek Guy: Oh, Ford Explorer. Yes, there we go.

Doug: Well, I’m thinking back to an episode we did with Dr. Ian Walker, who was talking about, you know, if purchasing a car was just about transportation, you would buy the cheapest, smallest, most fuel-efficient vehicle you could afford, and you wouldn’t really think about much else. You’d think about safety, right? That’s about it. But that’s not how we view cars. And that’s why so many people are in debt up to their eyeballs because they’ve bought the Escalade or something like that, even though they’re just one person driving to work, or maybe they’ve got kids they drop off in the morning. But they’re buying really expensive cars because it does signify status. And like I said about Los Angeles, but this is true almost everywhere else, it is the number one thing that they are presenting to other people in the school drop-off line, at the office. What you drive is the first thing most people see and know about you, and therefore make a lot of assumptions about who you are.

Derek Guy: Yeah, I have a buddy of mine who is really into cars. He has a bunch of them; he’s like a car collector. And every time we meet up, he’s in a different car, and he drops me off at, like, the local BART station. I personally don’t have a problem with, like, people that are, you know, into cars. I just don’t think that we should have to buy one to live. I think if that’s your hobby and you have the space and that’s, like, your—you know, your thing, you know, that could be fine. I just, I don’t personally want to buy a car, and I don’t want to have to live somewhere where my ability to get food and, you know, do basic things like run errands or ship packages is dependent on me being able to spend—I don’t even know how much a car costs anymore. I don’t know what people pay in payments and insurance or all that. But, you know, I don’t—I don’t even want to have to pay a dollar. So I just think it’s a shame that so many lifestyles are tied to your ability to transport yourself based on your ability to pay this fee.

Sarah: Right. And here’s where cars and clothes are different is that, you know, if you want to go to your local bodega wearing a sweatshirt and not very interesting jeans and whatever, you can do that. We allow people to dress how they want for the most part, but then we mandate essentially with our built environment that people drive to get where they want. If you—if you hate cars, you still have to deal with cars. [laughs]

Doug: Although I would argue there are some neighborhoods in the United States—and including here in New York City—where I just remember living on the east side of Manhattan, and friends who would not go out without getting full makeup on and wear something nice just to go to the bodega, because God forbid they run—God forbid they run into someone they know. But yes, it’s not—you don’t need it in order to get to your job, or there’s a lot more leeway. Derek, I was thinking—I saw your interview with Adam Conover, former guest of our show too, and you had a really interesting thought experiment about, you know, people say they don’t care about fashion, but if you said to a guy, “I’ll give you a pair of pink pants for free, or you can buy a pair of jeans for $50, $100,” they’d probably still pick the $50- or $100-pair of jeans. When I saw you make that reference, I thought—I think the exact same thing would hold true for cars. Like, “I’ll give you this little pink car and you can drive it to work, or you can spend $700 a month on a Ford F150 to drive to your job. Which would you prefer?” I think most people would choose, “Where do I get a loan? Let me do it.” Yeah.

Derek Guy: [laughs] Right. Yeah, I don’t know. I think some people would drive a pink car. But, like, let’s say if. I don’t know, if you could think of something totally, like, contrary to someone’s identity, I don’t even know what that would mean, unless it’s something really offensive on the car.

Sarah: It would be like making me drive an SUV.

Doug: In Brooklyn.

Sarah: In Brooklyn. Just to go to the bodega.

Doug: Yeah. Just to go here.

Derek Guy: I think people do—are keyed in to those kind of social messages of some consumer things. And I mean, clothes are a little bit unique in that they are closer to our sense of identity than anything else. They’re literally the layer that sits next to our skin, so I think that that is something unique to clothes. But I do think that some people, you know, do choose cars based a little bit on what they think it telegraphs about them in terms of identity.

Doug: You know, so we’re talking a lot about the built environment and culture and all that, and I also heard you say that, you know, we’re in this moment, you’ve said, where dress is increasingly disconnected from lifestyles and even possibly people’s identities. And earlier we were talking about the kind of urban-suburban blandness and sameness that happens with new development that people often complain about. There seems to be a kind of bland sameness with cars.

Derek Guy: Yeah.

Doug: Back in the heyday of the 1950s, let’s say, the 1960s, cars were really interesting objects. They’re in museums now. It’s hard to imagine too many of today’s motor vehicles being in a museum 50 or 60 years from now because they’re all the same. The same color palette, the same rounded designs. And I wonder if we’ve just become so disconnected from time and space because of the expense of cities, internet culture, things like that, that’s having this effect on fashion, and by extension, I guess, car design.

Derek Guy: Well, my understanding—again, I don’t know anything about cars. I don’t own one, and I don’t drive one, and I don’t—it’s not my hobby. But my understanding from having friends that are into cars is that the homogenization and the blandness of car designs now has to do with safety protocols and rules and regulations.

Doug: Yeah, that’s a big part of it.

Derek Guy: Right. You can’t make those cars of the 1950s, which I agree aesthetically look better, in my opinion. My understanding is that you can’t make those now because they’re essentially death traps. So that all of the regulations has pushed us into this singular design. One of the weird things to me is that, to give an example, the Cybertruck. A couple months ago, I saw my first Cybertruck. I’m not—I’m genuinely not saying this for political reasons or, like, I’m not being a hater, but it was genuinely, I really thought, ugly. I really thought that it looked like the trash can inside bathrooms. Yeah, it was really ugly. The only redeeming thing that I can think about it is that if you dressed a certain way, if you dressed in this very futuristic Mad Max kind of way, and you got out of the car, then it could possibly look good because it’s such a brutalist kind of like, design. But a lot of people stepping out of that are wearing, like, basic business casual, and that’s just such—it’s already kind of a jarring, ugly design, in my opinion. But then for you to step out in this kind of like, aesthetic that has no connection to the brutalist aesthetic, to me makes it even uglier.

Derek Guy: And that’s kind of the weird thing is that there’s so much stuff is, like, hurtling towards this kind of same kind of, like, there is, like, a very bland car design that fits into this bland fashion aesthetic. To me, it all kind of fits into this aesthetic that I just don’t think is—I mean, who knows? Maybe in 50 years there’ll be, you know, a teenager kicking his legs up in the air and looking at these photos and saying, “I was born in the wrong era,” but I just don’t think it looks as good as those, like, 1950s car designs and whatnot. And yeah but, you know, I mean, if it’s for safety regulations, then totally makes sense. I do think that a lot of the new cars are kind of ugly, though.

Doug: So we’ve been talking about New York, and we’ve been talking about big marquee cities. You know, at the top, I mentioned Milan, you’ve been talking about San Francisco, Tokyo. What are some other less well-known or smaller cities I should say that you think of as really good fashion centers or places where you can go and find really iconic style?

Derek Guy: I mean, this is kind of a weird thing because I do think that there is a—on average, there’s a lot more interesting fashion, for example, in New York City, in Tokyo, in London, Paris. I tend to think that walkability in urban design is very linked to interesting fashion. But I also think that smaller, let’s say, like, secondary cities are still interesting in that as long as you’re tuned—and I don’t mean—I’m not saying this to be politically correct, but honestly, I do think that fashion is always going to be somewhat interesting if you think of it in terms of social language, because you get to see how different groups dress and signal their identity. You know, if you’re in Florida and in Miami or something, you get to see, like, Cuban communities and how they dress for, you know, kind of like, partying or weddings or, you know, like weekends. I think that is interesting. When you go into LA, you tend to see people who are much more, like, trend driven. But, you know, that can also be its own sociological thing.

Derek Guy: I think fashion is always interesting as long as you think of it in terms of social language. But it is true if we’re just talking about, like, pure styles, I do think that, like, the kind of major urban walkable areas like Paris, Milan, London, New York City are stylish. I did a podcast interview once with Avery Trufelman, and when we were off air, she was like, “So being into clothes, are you, like, disappointed all the time with what you see in San Francisco?” And I was like, “Gosh, no. Like, obviously not everyone’s, like, super fashionable, but I can’t walk down the street without seeing a stylish person, like, once every 30 seconds or so.” So to me, like, anytime you’re in any of these cities, you see a stylish person. You just have to open your mind to, like, how young people are wearing vintage clothes, and how musicians are putting together outfits and all that stuff. To me, it’s always, always interesting and cool how people are putting things together.

Doug: That’s a great place to wrap it up. Derek Guy, thank you for joining The War on Cars.

Derek Guy: Thank you so much for having me on. This was a pleasure. And thank you to your audience for putting up with my cat’s meowing.

Doug: We’ll have the cat back next time.

Derek Guy: [laughs] Exactly. Exactly. Thank you.

Doug: So that’s it for this episode of The War on Cars. Once again, thanks to Derek Guy for joining us.

Sarah: The War on Cars is supported in part by the Helen and William Mazer Foundation and by listeners like you.

Doug: Very NPR of you. I liked that read. That was great.

Sarah: [laughs] Go to Patreon.com/thewaroncarspod, and sign up today for exclusive access to bonus content, ad-free versions of regular episodes, presale tickets for live shows, free stickers and more.

Doug: I am not as NPR as you are, so I’m just gonna read this part normally for me. A big thanks to everyone who supports us on Patreon, including our top contributors, Charley Gee Of Human Powered Law in Portland, Oregon, Mark Hedlund and Virginia Baker.

Sarah: Also, a big thanks to our sponsor, Cleverhood. You can find all of their cool gear at Cleverhood.com/waroncars[https://cleverhood.com/pages/thewaroncars].

Doug: And a reminder, tickets are now on sale for our Patreon supporters for our show in Minneapolis in April. And we’re being brought out there by Our Streets. We’ll put a link in the show notes. This episode of The War on Cars was edited by me. Our theme music is by Nathaniel Goodyear. Transcripts are by Russell Gragg. I’m Doug Gordon.

Sarah: I’m Sarah Goodyear and this is The War on Cars.

Derek Guy: [cat meowing] Sorry, give me a second.

Doug: Yeah, it’s all right.

Sarah: Don’t worry.

Doug: The cat is a special guest.

Sarah: Keep—just as long as she’s okay. Just, you can feel free to keep talking.

Derek Guy: This is the loudest she’s ever been, unfortunately, and I apologize.

Doug: The cat is a fourth guest. Fourth host. Yeah.

Derek Guy: [laughs] I don’t know how this cat would ever survive out in the wild.

Doug: [laughs]

Derek Guy: She just, like—like anytime she experiences any kind of loneliness or discomfort, she would just make noise and then just get eaten by, like, a tiger. Like, I don’t even understand. Like, how does that work?

Doug: Yeah. This cat would not survive A Quiet Place, the movie.

Derek Guy: She should be dead within, like, 10 seconds. Crazy!

Doug: [laughs]