Derek Guy doesn’t know what to make of his newfound fame.
The Canadian-born men’s wear writer – better known as “the Twitter men’s wear guy,” or by his handle, @dieworkwear – has become ubiquitous on the social-media platform now called X. His informative threads on men’s fashion and acerbic takedowns of Internet trolls are seemingly on everyone’s feeds whether they follow him or not.
On any given day, it’s common to see his posts opining on the clothing choices of politicians and other public figures, delving into the historical context behind certain looks, or giving detailed threads dispensing advice on how to build a wardrobe, find shoes that fit or dress as a larger male figure.
A dressed-down Conservative Leader Pierre Poilievre? “This makeover looks like what house flippers do to homes.” Former Toronto Mayor John Tory in a suit jacket, skinny trousers and sneakers? A disjointed silhouette with legs “like popsicle sticks.” Psychologist Jordan Peterson in a tweed coat, satin tie, white dress shirt and light blue jeans? “This outfit would make sense if you’re meeting investors at an evening party after duck hunting at 3 p.m.”
Over a year and a half, Guy has gone from relative unknown to a reluctant influencer, with about a million followers on the platform. Users frequently tag him in posts, seeking comments or advice. After skewering the attire of English media personality Piers Morgan and Conservative pundit Ben Shapiro, both invited him on to their television shows – invitations he politely declined.
The attention is somewhat unnerving to Guy, who, for a decade up until 2022, posted mostly about niche Japanese workwear brands and inside jokes to a small group of fellow men’s wear enthusiasts.
“I was actually really anxious about it for a while because I’m a really private person,” he said in a phone interview from San Francisco, where he now lives.
He declines to offer many details about his upbringing or to be photographed for this story. But he shares that his parents were refugees of the Vietnam War, who hopped from country to country in search of work, taking him along for the ride.
As an adolescent, Guy befriended Polo Ralph Lauren enthusiasts called Lo-Heads, whose style originated in the late 1980s in New York and by the early 1990s spread to California, where he would admire the aesthetic of the best dancers at his favourite clubs. He discovered mid-century jazz and French New Wave films, both of which cultivated in him an appreciation for men’s tailoring that he began to blog about in 2011.
His blog name and X handle, Die Workwear, began as a playful jab at the popular heritage men’s wear look of men dressing like lumberjacks, said Guy, who now laughs that he’s stuck with “a really stupid name.”
He attributes his explosion in popularity to a series of online events. In November, 2022, Dave Portnoy, the polarizing founder of the bro-centric sports blog Barstool Sports, announced that he had started his own watch company. Guy reposted the announcement with screenshots from Portnoy’s website, commenting that it was “shameful” to sell timepieces with $42 quartz movements for $2,400.
The post gained traction, with responses including an eight-minute video reply from Portnoy in which he lashed out at “watch dorks” and haters. Another person commented that the hefty markup of Portnoy’s watches was no different from what luxury brands do with cashmere sweaters, prompting Guy to respond with a thread about how cashmere is produced and the difference between low- and high-quality knits – the kind of explainer that he would come to be known for.
“I had had a few viral tweets in the past, but they were usually jokes,” he said. “This was the first viral tweet that was me breaking that jokey character and saying, ‘Here’s something I think is informational.’”
A few weeks later, the social-media platform, then recently acquired by Elon Musk, introduced a “for you” tab – an algorithmically curated feed of posts, apparently inspired by the TikTok feature of the same name – that inserted the men’s wear writer into seemingly everyone’s feeds.
Over a few months beginning in late 2022, his following on the platform doubled to around 100,000; he’s now at about a million. With his new readership, Guy has been more careful with his posts, reining in criticism that could be seen as mean-spirited to the average follower, instead setting his sights on self-described “alpha-males” like Andrew Tate, politicians and other public figures.
While his avatar is an illustration of the late U.S. lawyer and Republican politician Elliot Richardson, whose style of dress he admired, Guy is more interested in the minutia of perfect pants than politics, though some have taken to ascribing beliefs based on his skewering of right-leaning figures.
“The man has some great sartorial insights, but one suspects he is a lib,” wrote American political commentator Michael Knowles.
The most meaningful feedback he has received to date has been from people who found his advice useful, such as the men who chose wedding suits based on his insights. His mother, a fan of American celebrity culture, has also gotten a kick out of his growing popularity. (“I told her Meghan McCain’s husband yelled at me, and she went, ‘Oh, wow!’ That made her happy,” he said.)
But asked whether he might parlay his newfound fame into business opportunities, Guy said he’s uncomfortable with the idea of self-promotion. He has been approached about authoring a book – an endeavour he is considering to make his mother proud.
“She feels that it’s prestigious,” he said. “So, there is a part of me that wants to do that and then put it in her hands.”