Interview With Derek Guy, X’s Viral Sensation
Suits, Tweets, and Sartorial Feats: Interview With Derek Guy, X’s Viral Sensation

From sharp tailoring critiques to digital fame, Derek Guy is Twitter's style sheriff, roasting fits and guiding the fashionably lost, one tweet at a time

Picture the internet as the Wild West. On one side, you've got the regular townsfolk scrolling in peace, and then there are the (bad) cowboys, armed with snark and insults. But right in the middle stands Derek Guy (@dieworkwear), a sartorial gunslinger with a sharp tongue and even sharper tailoring critiques. He’s not here for your family; he’s coming for your wardrobe, whether you’re Andrew Tate or the U.S. national hockey team. 

Over the past year, Derek has become an unavoidable fixture on X feeds. Whether you’re a fashion enthusiast or just curious why everyone’s quoting savage critiques of Oxford shirts, he’s there, algorithmically lodged in your “For You” tab like an unskippable ad. Despite the fame, he’s stayed true to himself, nerding out over suit cuts and waxing poetic about loafers. 

 

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His style? A blend of deep fashion knowledge and biting humour. One moment, he’s dissecting the downfall of slim-fit jeans; the next, he’s roasting a politician’s tragic tie. But with fame come headaches; Derek’s baffled by the influx of comments from folks who clearly don’t care about fashion. It’s like going viral for being the last guy on Earth still debating cufflinks while everyone else is in joggers. 

Yet there’s sincerity in his approach. He’s not trying to be the next big influencer; he’s just exploring the stories behind clothes, from heritage brands to why your dad’s old blazer is suddenly cool again. For a guy who loves “nice little outfits,” he’s somehow become Twitter’s sartorial conscience. Agree with him or not, you can’t deny he’s got style, both in his words and his wardrobe. Man’s World India spoke to him about menswear evolution, fashion missteps, and his most treasured pieces. 

  

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You’ve been writing about menswear for 15 years. Where do men struggle most in dressing? Is it just about finding the right size? 

Derek Guy: I think of dressing as a kind of social language. Everything hinges on the cultural context and the dress norms that you're in. When I talk about clothing, let's say on my Twitter account, I often pull a photo of someone trying to wear a suit in a specific way. I assume they’re trying to wear clothes in a way that reflects their background and worldview. Of course, there's no way to know for sure, but I usually assume it's about someone. Under those specific ways of dressing, there are certain ideas about fit and proportion, which aren’t universal. For instance, if you were into skate or 1990s rave culture, those clothes tend to be baggy and fit differently. To me, it’s about understanding the social context of clothes, the social practices, and the message you want to send when getting dressed. 

So, to answer your question, I think where men struggle is that they either don’t think about the social language of clothes at all—just throwing random things together—or when they try to dress better, they think there’s only one correct way to dress and adhere to rigid rules. If they consider clothes as a language, they can develop a real style instead of approaching it mechanistically. 

  

Have you seen menswear become more adventurous recently? 

There are many ways to answer that question. I’d say the discussion has become a lot more diverse. In the early 2000s, as the online conversation about fashion and menswear began, much of it was focused on women’s wear because it was a larger space. For menswear, a couple of narratives emerged. In the U.S. during that time, one narrative was the metrosexual look. Coming out of the '90s, where baggy clothes were associated with masculinity, some men started wearing much slimmer clothes. Some even ventured into the women’s aisle for skinny jeans and slimmer shirts due to the lack of slim-fit options for men. This metrosexual narrative led to questioning masculinity and sexuality, suggesting that men who cared about their appearance might not be "real" men. 

Then there was the Heritage Movement, which emphasized that men were dressing too casually and needed to invest in timeless classics—think buffalo plaid shirts, tweed jackets, work boots, and raw denim jeans. Shows like Mad Men reignited interest in tailoring. From 2000 to 2010, these two narratives dominated. The metrosexual narrative suggested that some men were interested in fashion, while the heritage narrative encouraged a more traditionally masculine style. 

By 2013-2015, people were growing tired of both workwear and tailoring, shifting focus to streetwear and designer clothing. Now, in 2024, there’s no single dominant narrative. The early 2000s had a clear message: invest in classics, dress like your grandfather. Today, it’s more about individual exploration, but that lack of a guiding narrative can confuse newcomers to fashion. 

This shift has also led to what Cathy Horyn called "The End of Trends." She wrote that in the 1990s, people looked to fashion editors for direction, while now, the internet allows individuals to curate their feeds and follow niche trends that suit them. There are countless micro-trends, and what's popular in one community might not even register in another. 

  

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Why do men have gender anxiety about fashion? Are we moving towards gender-neutral menswear? 

It’s a little complex. Clothing in Western society is considered frivolous, and an interest in fashion has historically been associated with femininity. This dates back to ancient times; Greek philosophers and later thinkers like Karl Marx used the term "fashion" negatively. There’s also the famous tale of "The Emperor's New Clothes," in which the emperor is mocked for being vain and obsessed with his appearance. 

Since fashion has been linked to femininity, many men shy away from it, fearing they may appear less masculine. The trial of Oscar Wilde, for example, solidified many stereotypes we hold about gay men today—witty, flamboyant, and fashion-conscious. This trial etched a strong association between being fashionable and possibly being gay, making many men wary of appearing "too fashionable." 

Tom Wolfe once wrote that men would rather be seen in public with a pornography magazine than a fashion catalog. He was exaggerating, of course, but he made a point that an interest in fashion was seen as a "secret vice." The cultural pressure is strong, and even today, many men hesitate to experiment too much for fear of judgment. 

As for gender-neutral fashion, there have been movements toward it before, like in the 1970s. Men and women wore bell bottoms and floral shirts back then, but true gender-neutral styles never fully took off. Interestingly, these experiments sometimes reinforce gender differences rather than blur them. A woman in a large man’s trench coat might look even more feminine, while a man in a woman’s blouse could appear more masculine, depending on how he carries it. Gender, style, and the meaning of clothing are always evolving, and what’s considered gender-neutral today might shift in the future. 

  

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What’s the most misunderstood aspect of menswear today? Why does it remain niche for many? 

I think the most misunderstood aspect of menswear is that many see it as just consumerism and high fashion. To me, it’s also about how everyday people dress. Fashion isn’t just runway shows; it’s about how people throughout history have dressed, from sailors in the 1960s to local trends in different communities. It’s a sociological subject, reflecting our culture. Many dismiss it as frivolous because they only see the high-fashion side, but it's much more than that. Understanding the cultural and historical context of clothing can make it a rather fascinating topic. 

  

You’ve said fashion isn’t just for slim guys. How can someone self-conscious about their body try new styles? 

Everyone is self-conscious about their appearance to some extent, not just larger guys. Short men, tall men, muscular guys—everyone has their own insecurities. The challenge for bigger guys is often finding clothes that fit well since most ready-to-wear options cater to average body types. This can be discouraging because you can’t see how something looks if it doesn’t fit properly. I’d suggest finding solutions to your specific fit challenges and then thinking of dress as social language. 

My friend, for example, is a larger guy who mixes tailoring with workwear. Tailoring can be tough for bigger guys since it might require custom tailoring, which is expensive. However, workwear and vintage clothing, which tend to be cut larger, can be great alternatives. Clothing from before the 2000s fit looser, so exploring vintage shops can yield good results. Ultimately, find what fits your budget and style, and use that as a way to express yourself. 

  

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What’s one menswear trend you hope never fades, and one fashion faux pas you’d forgive? 

I don’t really follow current trends, but I’ve noticed a shift toward looser clothing. After 20 years of slim fit, I hope classic fits remain available. It’s great to have options for both slim and baggy looks, but for someone just starting, middle-of-the-road options are often the easiest to work with. As for fashion faux pas, I’m willing to forgive anything as long as someone is genuinely enjoying their clothes. If they feel good in what they're wearing, that’s what matters most. 

 

If you could dress a modern celebrity, who would it be, and what would you put them in?  

Any U.S. hockey player—those tight suits and flashy ties need fixing. I’d show them how a better fit can make all the difference. 

 

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Is there a piece of clothing you cherish? 

Not clothing, but the piece in my wardrobe that means the most to me is my father's Rolex. It's a Rolex Oyster Perpetual Datejust on a Jubilee bracelet. My dad's family is from Vietnam, and he bought this watch for himself as a university graduation present sometime in the late sixties. After he graduated, he went to work, and then the Tet Offensive happened, which is when the North Vietnamese were able to break into Saigon, where my family is from. The North Vietnamese were eventually driven out, but many people realized that the end of the war was near, and my parents, who were based in Saigon, understood that bad things were about to happen. They made plans to flee the country. 

My dad bought a fake passport from someone and posed as a university student because he had just graduated. To pose as a student, he had to pretend not to have much on him, so he bought a cardboard box and opened each layer, putting in thin gold sheets and taping the layers together before filling the box with books. If someone at the border stopped him and felt how heavy the box was because of the gold sheets, they would see just school books inside. That was his plan. The only thing he took with him was this Rolex, which was one of the few items he had from his past life. 

He went from Vietnam to Cambodia, where there were the killing fields, then to Iran, and finally to Canada, where there were no more revolutions. Throughout my life, I had always seen that watch on his wrist. I don't think I've ever seen him without that watch, to be honest. Looking back, it’s significant that when I turned 30, he met me in the hallway of our home, took off his watch, and gave it to me, saying, "I want you to have this." That is by far the most meaningful thing that I own, not only in my wardrobe but of all my possessions. 

It reminds me of where my family came from and the sacrifices they made, as well as the difficulties they faced. It represents the strength and character of my father. My mom and dad mean everything to me. When I think of my father's journey from Vietnam to Canada, and the challenges he faced, it makes me appreciate that watch even more. It’s amazing that it still works, even though he bought it in the mid to late 1960s. 

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