The viral 'Twitter menswear guy' just wants an affordable home in a walkable neighborhood

• Derek Guy, a California-based fashion writer, has become a menswear influencer on X.
• But increasingly he's used his massive platform to opine on the nation's housing crisis.

If you've spent any time on X recently, you've likely encountered a certain viral account — or seen other users complaining about the dominance of said account. It belongs to San Francisco-based fashion writer Derek Guy, also known as the "Twitter menswear guy" behind the @dieworkwear account.

Guy, whose following has ballooned from 25,000 to 600,000 since late 2023, is best known for his love of Italian tailoring and his pithy critiques of celebrities' ill-fitted suits. But, increasingly, he's been sounding off on his other passion: affordable housing.

San Francisco's housing crisis became personal for Guy when his rental apartment was sold, and its new owners forced him out in order to move in themselves. His subsequent search for a new home in the city was a wake-up call. He remembers viewing a tiny, windowless basement unit alongside an older woman and two day laborers willing to squeeze into the apartment together, among a long line of others.

"I was thinking, I don't want to push an old lady out of a potential unit, this is ridiculous, but I also can't be homeless," he told Business Insider.

As a freelance writer and blogger, Guy can't imagine accumulating enough savings to buy in a city where median home prices are far north of $1 million.

"I'm probably never going to be able to afford a home in San Francisco, that's my guess, or anywhere in the Bay Area, unless I move really, really, really far out," he said.

His housing journey is a far cry from his parents' experience of arriving in North America as war refugees from Vietnam, working as a janitor and a secretary, and buying a home within a few years.

On the face of it, housing affordability has little to do with fashion. But Guy has written about how diversity in cities — made possible by affordable housing — is essential for creative inspiration. For instance, fashion designers constantly pull ideas from streetwear.

He pointed to clothing lines like Maison Margiela and the Japanese brand Kapital, which is inspired by "ragamuffins," Guy said. Related: Tokyo has long kept housing abundant and affordable, which has allowed all kinds of people, including artists, to stay in the city.

"That only exists because the designer saw that and thought it looked cool," Guy said. If cities are too expensive for a diverse array of people to live in, that inspiration dries up. To fight gentrification, he says, the city needs to build a lot more diverse types of housing.

"All of the stuff that I think is cool and makes the city interesting involves affordable housing," he said.

Walkable communities are expensive because they're in high demand, and they're in high demand because people like living in them. Guy, who hasn't owned a car in decades, knows what the research shows: that living within walking distance of a grocery store, a coffee shop, or a public park boosts happiness and wellbeing. He loves to point that out.

"Stop thinking you need a relationship to be happy. Sometimes all you need is affordable housing in a walkable neighborhood where you can wear nice little outfits and get food," he posted on X last fall.

It's infuriating to Guy that San Franciscans protest a new four-story apartment building or even residential high-rises as thousands sleep on the street. The city needs more dense housing of every kind, both market-rate and affordable, he argues. Guy's a believer in the laws of supply and demand — the more housing, the lower the cost — but also wants the government to provide homes for those in need.

"I would love a skyscraper literally in my backyard that I can buy a home in," he said. "I'll admit, some of the stuff that's proposed by YIMBYs I think looks ugly, but I don't care anymore. You could paint a clown face on a building and I wouldn't care because we're just in a crisis."

The Yimbyland — an acronym that stands for "yes in my backyard" — X account recently declared Guy "the world's most fashionable YIMBY" and pitted him against economics writer and well-known YIMBY Matthew Yglesias in a tongue-in-cheek "Developer Shill Bracket."

Despite despairing about the state of housing, Guy tends to keep his posts about it light.

"Kate her this. Kate her that. How about you CATER to renters who want you to build housing," he wrote of "#KateGate," the conspiracy theories around the Princess of Wales' disappearance from the public eye. "Middleton this Middleton that. How about you put me in the middle of a ton of affordable housing."

He's wary of wading into messy, unproductive debates between conservative NIMBYs, leftists, and YIMBYs on housing Twitter.

"The fights just seem so nasty for no real reason when the real enemies are people who are stopping development in these increasingly wealthy communities," he said. "The only thing that I disagree with is not building housing and sprawl."