Clothes may make the man — but they really make the city.
Perhaps that’s how (or why!) menswear icon Derek Guy transformed his vast social media platform into a megaphone in the ongoing culture war over the simple pleasure of walkable, sprawl-free communities.
Guy didn’t set out to become a prominent voice in urbanism, let alone one of the leading arbiters in men’s style. The Canadian-born menswear writer, known as @dieworkwear on Twitter, has amassed more than 1.2 million followers for his threads on the intricacies of hand-knit sweaters or the crassness of contrasting buttonholes while dunking on politicians for wearing ill-fitting suits and ugly dress sneakers.
But Guy has used that perch to share with a mass audience his beliefs about why Americans should end their dependency on cars and embrace the joy of walkable neighborhoods. And when a menswear writer wades into the urban space, it resonates well beyond planning and zoning meetings.
“Most people are not menswear nerds, but they may be nerds about something else like baking or baseball and if you think about it, what has happened to cities affects you in some way depending on what passion you have,” Guy told Streetsblog. “It might be about the monoculture or lack of diversity in cities or how much money you have left over because your rent is so high.”
Fashion and urban planning have more in common than you'd think at first glance.
Sure, a transportation planner might don a deep-pile Patagonia fleece, baggy wide-wale corduroy pants, and a pair of New Balance 990s while prowling a farmer’s market. But Guy argues that catering to vehicles in communities where housing is unaffordable has unintended consequences. It has made it more difficult for tailors and shoemakers to afford their shops, for one thing. And it has contributed indirectly to the spread of bland business-casual attire that has afflicted workplaces across the country.
“If you had more walkable neighborhoods and you had more tailors around, your effort level would decrease because more options would be available to you,” he said. “You wouldn’t have to read people like me online who tell you, ‘Oh your pants should fall in a certain way.’ You would go to a professional, and they’d fit it for you.”
Guy grew up with a fondness for cities and lived abroad in Moscow before settling in the Western United States (he has become more private about his personal life as his audience has grown and wouldn’t say where he lives, although he allowed that he hasn’t driven a car in more than a decade and mainly walks or takes the bus).
He began reading menswear blogs and online forums in 2007 and launched his own blog a few years later where he conversed with other clotheshorses and wrote in-depth posts about tailoring, Ivy Style, and craftsmanship.
But it wasn’t until he traveled to Italy in 2012 that he learned about the pleasures of living in an old-world neighborhood where cafes and haberdasheries were a leisurely jaunt away. Guy was particularly charmed by Naples, where people hung laundry in its Spanish Quarter and he happened upon a two-person family business that made single-stick umbrellas by hand.
“The Spanish Quarter was pretty affordable, where people were living with less economic means, and you could walk to Chiaia, a ritzy district with expensive shops,” Guy said. “To me that’s ideal to have people living in different economics classes and have walkability because it makes for a pleasing living experience.”
Soon he began inserting jokes about walkable neighborhoods in his blog posts and social media missives along with references about niche Japanese brands. Guy grew his Twitter following to 50,000 by October 2022, when the social media company began tweaking its algorithm before debuting a “For You” tab two months later.
Suddenly, Guy’s Twitter threads on how to buy a high-quality cashmere sweater and a post chiding Barstool Sports founder Dave Portnoy’s start-up watch company unexpectedly went viral because they were seen on millions of people’s Twitter feeds. By the end of 2023, he had 500,000 followers on Twitter. Now he has 1.2 million with another 115,000 followers on Instagram.
Transit leaders appreciate Guy’s ability to make complex arguments about the dangers of sprawl easily digestible to a mass audience.
"I’ve been following Derek for a long time, and I wasn’t surprised at all that walkable places are important to him,” said Abi Araya, a spokesperson for Smart Growth America. “To me, this is just another example of how transportation options provide so many benefits. That’s why all kinds of people want those options to exist."
Even though his audience has grown by a factor of 25, Guy hasn’t shied away from explaining the intricacies of craftsmanship or what makes a politician’s outfit an incoherent mess. He has also leaned into promoting walkable neighborhoods while explaining the disastrous effects that catering to cars have had on our cities … and our wardrobes.
He believes that Americans stopped wearing hats and longer overcoats in the mid-20th century because we became car dependent and drivers didn’t want their hems touching muddy car mats or having their coat drag when they sit down. And our clothes don’t fit as well because there are so few knowledgeable tailors who can afford to rent a shop in a city whereas in Tokyo, there’s a robust ecosystem supporting tailors, shoemakers, and other craftsmen because rent is relatively cheap.
“Japan has a much richer [fashion] scene because the cost of living is so low,” Guy said. “You don’t have to sell thousands of shoes to pay for a storefront, you only have to sell a couple dozen shoes a year to pay for that life.
Guy has been dismayed that conversations around car ownership and walkable neighborhoods have become fodder for the culture wars while rent continues to rise faster than wages and little new housing gets built.
He hopes that people can experience the joys of living in walkable neighborhoods, one of which is to show off their outfits when they go out for an errand or to meet their friends. They may even begin to dress better, too.
“You choose clothes because you dress to be seen, and to be seen is what it means to dress well,” he said. “The motivation of putting on a nice outfit is lower when you transport yourself in one box to go to your office and you go back to your car and go back home. I like being able to wear a nice outfit, go for a walk and get a little exercise in.”
