Why Twitter’s Favorite Menswear Guy Can’t Stop Talking About Affordable Housing

Since 2011, Derek Guy (@dieworkwear) has built his audience of one million followers on X (formerly Twitter) through iconic viral moments like threads outlining how to buy a high-quality cashmere sweater, or perhaps more scandalously, roasting the annoying conservative pundits for their poor wardrobe choices. However, it seems the goal of his account is to help the masses dress their best: he discusses the nuances of well-tailored suits, styling with accessories, dressing well for all body types, caring for clothes, and finding affordable vintage pieces on eBay.

But Guy, a San Francisco resident, also uses his platform to slip in his thoughts on cities. Perhaps it’s an unexpected turn away from his fashion-forward brand, but as a self-proclaimed pedestrian and public transit user, his urbanist-oriented quips range from tongue-in-cheek pop culture references to perusing Zillow in other cities for "walkable neighborhoods." While Guy (his real name) prefers to keep some of his life private (including his age and profession beyond his fashion writing), Dwell spoke with him to learn more about how he connects fashion with affordable housing—and what to wear on a sweaty work commute.

Even though this is an interview about urbanism, I have to know: How did you get interested in men’s clothing?

When I was young, people were into clothing as an auxiliary thing to a primary interest. If you’re into punk, you dress like a punk. I was really into hip-hop music and going to dance clubs. At the time, there was this emergent dance called freestyle, and the scene was basically populated by guys who wore Nautica, Timberlands, Tommy Hilfiger...but the most stylish guys were wearing Polo Ralph Lauren, head to toe. And this was a look that was known as "Lo Heads." 

I got interested in clothing through a music scene, and then became interested in classic clothing through Ralph Lauren. To me at the time, it was a streetwear look. But Ralph Lauren presents his clothes in a way that makes you feel like you’re walking through John F. Kennedy Jr.’s personal wardrobe. It’s very stylized. Through that, I learned who makes the original Oxford cloth button downs, and who makes the best tweed jackets, where the chambray shirt came from. Just like hip-hop introduced me to soul, jazz, and funk, Ralph Lauren introduced me to the language of classic clothing.

The music scene is pretty paramount to urban life. Did clubs shape how you think about cities?  

I was interested in dance music, which obviously entailed going to clubs. But I was also interested in graffiti art and a leftist kind of politics, and all of that entailed this kind of romantic view of city life. I spent time in public parks where there were mostly Black radicals, or at least non-white radicals, and the club scene was mostly populated by ethnic minorities. I’m Asian myself, and I just had a view of cities being very diverse places where you could hang out in parks and talk to people about various ideas. 

Also, I was into chess, so I spent a lot of time going to cafes and parks to play chess with older dudes. I went to train yards because I was into graffiti. Everything that I liked doing was in the city, and I imagined a certain kind of lifestyle where I could just read books and go to cafes, talk to interesting people, play chess, and go to music events. That’s what I thought the majority of my life would be like.

And now you live in San Francisco—did this romantic vision come to be?  

Every time I’ve moved my rent has skyrocketed, and over time, I’ve had to work more and more hours to pay rent, and that doesn’t leave a lot of time to do all the things I like doing. Also, the things that I like doing have disappeared from the city. I don’t want to make too much of it, because I’m also not the type of person who thinks that certain people shouldn’t move into the city. But, for example, in San Francisco, the Mission used to have a very lively nightlife, and as the area has become increasingly gentrified, it’s become quieter. Over time, it’s just become increasingly cheese and wine shops, expensive clothing stores, and then me spending a lot of time working to pay rent and not having enough time to even go to the museum. It makes me wonder, why am I even living in a city? 

Affordable housing is undeniably political, especially in San Francisco, where homelessness has become a lightning rod issue; and only recently have we had a broader political awakening around the politics of fashion. How do you connect these issues culturally? 

My feelings on homelessness have been shaped by writers like Mike Davis, who wrote an essay in the UCLA Law Review called "A Logic Like Hell’s: Being Homeless in Los Angeles." He writes about how cities deal with homelessness by making things harder on unhoused people so they can’t sleep in a certain area; they pass anti-vagrancy laws. I understand that [homelessness] is bad for business, but to bring it to fashion: I remember a store in San Francisco that sold a line that I love called Kapital—a Japanese brand that riffs on workwear in America. The store was complaining about local homelessness. But if you look at Kapital, the clothing styles are almost identical to the "gutter punks" who populate Telegraph [Avenue] in Berkeley. And the store in San Francisco was selling $400 shirts, coats that can be $1,000. It’s such crazy irony that you are selling clothes that essentially borrow from the cultural capital of these people, but then push them out of the city. The whole reason this line is appealing is because it kind of embodies this idea of not conforming to the establishment. I just don’t think that pushing a person further and further to the outskirts helps anyone except a comfortable class of people that happen to have money. I feel that we should make services and build more housing and more affordable housing.

It sounds like your passion for affordable housing stems from cities’ ability to create and nourish subcultures, not just rip from them.

Fashion designers have been borrowing from various subcultures since the beginning of time, and these subcultures often, although not always, are based in cities. Vivienne Westwood was riffing off of alternative styles that, later on, morph into punk. I just feel that as cities become more homogenous and more taken up by only one class of people, they become intellectually less interesting, and that’s going to affect everything. It’s true certainly in fashion—which is not even in the top 10 most important reasons why cities should be vibrant. Fashion draws on the diversity of cities and the subcultures within them, and therefore we should have more diverse, vibrant places that will then inspire people to design.

So affordable housing might cultivate a stronger fashion scene…

Not just housing. We don’t have affordable custom tailors in San Francisco because the rent is insane. I know a guy in Florida, for example, that will make a pair of handmade, bespoke trousers. The long seams are made by machines, but the pattern making, cutting, top stitching—all of that is done by hand. And he sells them for $300 if you provide your own fabric. In San Francisco, if you were to get a pair of bespoke trousers made, it would cost around $1,500. You’ll never get the price of bespoke trousers down to $300 in San Francisco because of the high rents.

Something I would just like to see more of in the U.S.: I visited Naples [in Italy] many years ago, where you kind of get around mostly by foot. It’s so cliché; you know, on Twitter, people saying, ‘Oh, I went to Europe and it was so beautiful,’ and when they come back, they realize how walkable it was. But that was my experience: being able to walk around Naples, I found a small shop run by an uncle-and-nephew team—both the uncle and nephew were named Mario Talarico—and together, they made beautiful handmade umbrellas. And they were able to do it because the shop was small.

Before I let you go, I want to ask a pressing fashion question: If you were a cyclist, what would you wear to ride your bike to a work meeting and not show up disheveled? 

Despite talking a lot about tailored clothing on Twitter, I don’t actually believe that everyone should wear it. Obviously, cycling is going to wear down your trousers. So if you’re wearing tailored ones, that could be very expensive and not very economical. If you do wear tailored trousers, I would recommend things like whipcord or Calvary twill, which are materials that were historically used for horse riding and that will be more durable. You’ll also get sweaty, so in general—and this is more for shirts—linen dries faster than cotton. If you’re cycling in a linen shirt, when you arrive at the office, that shirt is going to dry a lot faster than a cotton shirt. You will have to deal with the fact that linen wrinkles a lot, so you could do a cotton linen blend. I would check out Proper Cloth; from memory, they have some quick-drawing dress strip fabrics. If I needed to look a little bit dressier I would just wear chinos. Then, for the jacket, if it was for something like a big meeting or ribbon cutting, I would probably carefully pack a tailored jacket.

Illustration by Agata Norwicka

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