Editor’s Note: This story originally appeared in Volume IV of B.H. Magazine. To get your copy (and access to future issues), subscribe here.
Spend enough time scrolling X (formerly Twitter) and it’s almost inevitable you’ll stumble across Derek Guy, better known to his 1.2 million followers as @dieworkwear – or more colloquially, “The Menswear Guy.”
Guy has become infamous for detailed X threads that read like excerpts from long-form essays, ranging from the structural tells of bespoke versus off-the-rack suits, to discussions about obscure Irish wool mills where one can invest in a handcrafted Aran knit.
His latest lark points out the sartorial foibles of public figures with scathingly polite accuracy. I pity anyone who sees the black-and-white sketch of the late US Republican and former Secretary of Defence Elliot Richardson – Guy’s avatar of choice – pop up in their mentions.
Concrete details of who Derek Guy is remain elusive, which is how he prefers it. After 15 years spent dissecting menswear forums, operating his own blog Die, Workwear, editing menswear blog Put This On, and contributing to publications such as Mr Porter and The Washington Post, he’s still managed to elude the millennial affliction of social media.
We don’t even know if he is a millennial, or what he does for a job. What we do know, however, is that Derek Guy is his real name. He’s Canadian, born to Vietnamese parents, and is now based in San Francisco. And that up until recently, he didn’t even own a smartphone.
“I’m just a private person,” Guy says as we settle in for our phone interview. We spent the better part of a fortnight negotiating a time that would suit his location. It turns out that, despite his prolific presence online, Guy only checks emails once a day and only transitioned from an old-school brick to a smartphone when his mobile carrier declared it obsolete.
“My carrier said they were doing some technological upgrade and that my phone would simply not work after a certain date,” recalls Guy. “So I found the cheapest smartphone possible. I’m actually a fairly frugal person outside of buying nice clothes.”
For all his resistance to the trappings of modernity, Guy is resolutely online. But his sudden saturation on everyone’s timeline, he says, was a peculiar quirk of the algorithm back in 2022 that unexpectedly force-fed his razor-sharp takes on tailoring into people’s ‘For You’ feed. It helped that he had a natural flair for good, old-fashioned smartarse snark.
“Yeah I’m ACAB,” he replied to one of his many detractors. “Asian Calling About Bespoke.”
“Growing up, my friends and I would bust each other’s balls all the time,” laughs Guy. He also jokes that he was born and raised on menswear forums, where: “Traditional tailoring is our native language and nitpicking was our culture.”
After a decade of tapping out evergreen articles like how a suit should fit or the best garment maintenance, Guy found himself wanting to branch out. “I just couldn’t write the fifteenth article on how a suit should fit,” he reflects. Like most of his generation, he’d been on Twitter since the early days of 2011. “I was writing a lot about culture and then trying to tie clothing in on Twitter,” says Guy. “I was making jokes – niche menswear jokes – up until 2022, and then my account started to blow up.”
The real explosion came when Guy critiqued Brick Watches from Barstool Sports founder Dave Portnoy, calling it a “rip-off.” The ensuing exchange, along with a detailed thread on cashmere production and the ethics of luxury pricing, catapulted him from a niche menswear writer to a broader audience. His following doubled almost overnight, reaching 100,000 by January 2023.
Recognising the shift, Guy leaned into his strength: educative critiques laced with gentle, venomous humour.
Trying to pick just one exchange or thread as Derek Guy’s magnum opus would be a Herculean task. But one stands out as a prime example of the depths he’s willing to go to make his point.
As with many of Guy’s musings, it began with a suit – a blue suit with garish contrast-stitched buttonholes worn by American right-wing mouthpiece Jackson Hinkle. Guy’s Twitter post became a lesson in how to tell if a suit was truly bespoke and “the many ways custom tailoring shops upsell or misrepresent their services.”
“I wasn’t trying to be blunt,” Guy says. “I just knew that suit was not bespoke. I wanted to double-check.”
This wasn’t the first time Guy’s dedication to accuracy became the focal point of online discourse. He recalls a separate incident when he wrote an article for Business of Fashion about the fall of Brooks Brothers. “My editor later left the publication and then she went on a podcast. The host said, ‘I saw that you worked with Derek Guy,’ and she said, ‘Yeah, he’s kind of weird. He’s really, really nice, but he’s kind of weird,’” Guy recalls.
“You have to imagine, I’m sitting here in my bedroom on my computer, and I hear that. It’s like overhearing a conversation where people don’t think you’re listening,” Guy pauses, letting the memory linger. “It was kind of hurtful, but then she was nice about it. She said, ‘Yeah, he’s a nice guy, but he’s kind of an odd person.’”
“I thought, well, maybe I am a bit weird.”
The Hinkle saga immediately rushed back into his memory.
“Hinkle claimed that his jacket was bespoke, and I didn’t think it was. I thought it was made-to-measure. So I found out who made the jacket and called the tailor. I asked all these questions about their process – how they do the buttons, how they draft the pattern – and I was like, ‘Yeah, it’s not.’ Then I went online and simply said, ‘No, it’s not bespoke,” Guy explains. “Immediately, Hinkle was like, ‘You’re just a hater.'”
“I said, ‘No, I got the information from your tailor.’ That blew up, and people were saying it was an insane thing to do. I didn’t think it was insane. But then that editor’s voice came back in my head, and I thought, maybe she was right. Maybe I really am weird.”
Weird or not, it highlights Guy’s knack for using fashion as the spark to fire up a debate around how little men know about the clothes on their backs, and that most men lack any real lexicon of fashion or understand its semantics. “I try to encourage people to think of dress as social language. What are the contours of that language and what do you want to express? But most guys don’t have any aesthetic direction.”
"the baseball guy is going to talk about baseball isn't he?" listen to yourself https://t.co/mCJt24d4hi
— derek guy (@dieworkwear) January 21, 2025
Derek Guy believes a lack of a dominant narrative this past decade has created genuine hurdles for men when it comes to building a cohesive wardrobe. It’s not that we don’t have a sense of style; we no longer know how to interpret it or speak its nuances fluently.
This, he explains, is never more apparent than when so-called “masculinity traditionalists” present themselves publicly wearing clothes that historically were coded as feminine. Like skinny jeans, which have become deeply ingrained into contemporary menswear. But when they first hit the market back in the early 2000s, they were considered “part and parcel of some broad decay in masculinity in Western society,” explains Guy. “There was a lot of hand-wringing over whether men were becoming feminine.”
It’s not all critique, either. Guy is quick to praise good style, good clothes, and great quality when he sees it.
Actor Colman Domingo has been regularly mentioned by him as one of the few men really pushing great personal style. Australian brand Etymology recently found themselves in a storm of international orders purely because Guy commented that he appreciated their shape and use of full-grain leather. And anyone accusing Guy of being culturally and politically partisan with his critiques, he’s openly said Republican politician Elliott Richardson is one of the best-dressed men in American politics.
Let’s also be very clear: Derek Guy isn’t saying you can’t wear skinny jeans. Or a skirt for that matter. He’s simply saying we have to learn the language. Which most of us did before the Internet metaphorically muddied the waters.
“If you were going somewhere, doing certain things and of a certain social status, you knew how you were supposed to dress,” he explains.
Many people, including me, like Colman Domingo's style. Beyond the high level of taste—meaning, the way he combines clothes—there's the matter of shape and drape. These clothes fit well, hang well, and have a distinctive silhouette. They're not just replicating his body. pic.twitter.com/3nA28IRPpY
— derek guy (@dieworkwear) February 26, 2025
“Over time the number of options started to explode, especially in the post-war period. People might go to Levi’s to get their workwear; they might go to Brooks Brothers to get their American tailoring; they might go to Armani to buy a kind of Italian Playboy outfit. And then, by the close of the century, you still had a lot of options, but people were still kind of tied to their subcultural identity.”
“[Today] there are all of these narratives of how to dress, and the Internet has made it so that it’s even harder. Dress has become more decoupled from people’s actual lifestyles and identities, and there are more options on the market. All this makes it harder to craft a narrative for all of fashion.”
This philosophy is in no small way inspired by Guy’s own formative years, learning the codes of style first-hand when he discovered the Lo Head subculture, which originated out of Brooklyn the mid-’80s and continued through the ’90s, whose aesthetic was built around Ralph Lauren.
“First you had the Lo Lifes, which were a crew that was sort of built around boosting Ralph Lauren, wearing Ralph Lauren,” Guy explains. “But if you were just into the look, you were a Lo Head. I had a bunch of friends who were Lo Heads and into this dance scene at the time.”
Guy says Ralph Lauren seemed to capture all the facets of menswear: preppy, tailoring, workwear and leisure. He still pays homage to this scene and the designer with a separate X account dedicated to the brand’s oeuvre, RL Goes Hard, which depicts archival shots of Ralph’s personal style and his brand. It also provides insight into how clothing can be appropriated and its legacy diluted, or even exploited, especially when it comes to streetwear and the way luxury houses have co-opted it into their collections.
“Streetwear used to be defined by what was happening on the streets,” Guy explains. “It was authentic, rooted in subcultures like skateboarding, hip-hop, and graffiti. Now, it’s dictated by corporations who have no connection to those cultures, often sold to people who are also not involved in street culture and will often call the cops on people who are.”
This disparity of fashion as it occurs across class systems is something that Derek Guy is also consistent in pointing out. “Class is an extremely important group marker,” he says. “Take the hoodie, for example. After Trayvon Martin’s death, there was a national conversation in the US about what it means when a young black man wears a hoodie. Clothing is never just about the garment; it’s about what people project onto it.”
Guy extends his analysis into the debate of walkable cities and affordable housing, arguing that these experiences and the future of retail are threads that are intricately intertwined. “I think shopping is horrible now because you have to research so much,” he says. “The ideal situation is neighbourhoods filled with hobbyist-run shops – places where enthusiasts, not profit-driven salespeople, guide you to what works for your lifestyle, while lowering the cost of real estate would allow for a more flourishing kind of luxury retail environment.”
“These issues are interconnected,” he says. “When people live in walkable neighbourhoods, they’re more likely to engage with their communities, support local businesses, and think about the long-term impact of their choices.” Guy envisions a future where small businesses thrive in urban spaces designed for people rather than cars.
“Fashion could play a role in this by fostering a sense of place and identity,” he says.
“Good clothes aren’t cheap, and cheap clothes aren’t good. But the industry needs to find a way to make quality more accessible without exploiting workers or the planet.”
If you’ve enjoyed this feature article on Derek Guy, consider a few more of our favourite stories – direct from the pages of B.H. Magazine:
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