Derek Guy has quickly become one of the most respected fashion writers largely for his pointed critiques of the sartorial blunders made by right-wing personalities. In 2025, he’s still stealing the show thanks to his massive digital footprint. In the time since, Guy has shot to stardom, gaining over 1.3 million followers on X (formerly Twitter). A year ago, in 2022, he was an under-the-radar menswear writer with 25,000 followers. His Instagram account, @dieworkwear, has turned into a platform for acute observations that mix sartorial savvy with political subversion.
Guy’s road to this moment began 15 years ago, when he first started engaging on menswear forums. He subsequently started his blog, “Die, Workwear!” In it, he comedically ridicules the tacky clothing and outside-their-body, wrong look of the poobahs of the MAGA movement. As a result, his critiques have frequently gone viral, inspiring the awe of supporters and the anger of detractors. Notably, he has pointed out the wrinkles on former President Donald Trump’s trousers and the “collar gaps” on Stephen Miller’s suit jackets, highlighting the intersection of politics and personal presentation.
Earlier this month, Guy shared his experience of being one of millions of undocumented residents living in the United States. This disclosure had been made public under the specter of violent far-right influencers and government officials threatening the safety of Vice President Kamala Harris. In a bold statement, Guy posted an image of a Men’s Wearhouse storefront on X, indicating where immigration agents might find him: “Here is my house.”
Guy provocatively shot back at a luxury time piece purveyor. This time, expanding to a class of 800 students, he wrote an award-winning, one-thousand-word cultural history which focused in part on how immigrants and refugees built the foundations of luxury watch manufacturers such as Rolex. His intellectual approach to fashion goes beyond the surface level aesthetics. It speaks to the theme of immigration and identity as a whole.
“Honestly didn’t expect this is what would happen when I joined a menswear forum 15 years ago.” – Derek Guy
This unusual path to success is what has made him a celebrity. More importantly, it shines a light on the challenges that undocumented immigrants face here in America. Guy shared insights into how his immigration status has impacted his life, stating, “The lack of legal immigration has totally shaped my life. It has made every interaction with the law much scarier. It has shaped which opportunities I could or could not get. It has taken an emotional toll, as this legal issue hangs over your head like a black cloud.”
Guy knows that as he faces these challenges, he just has to be brave enough to stand up and be counted. He recognizes that many individuals share similar circumstances and emphasized that “I know many people in my position and they are all like your neighbors.” His advocacy extends to addressing the harsh realities faced by immigrant families, noting that “the cruelty in today’s politics feels horribly corrosive.”
Guy’s commentary goes a long way in unpacking the hysteria that characterizes immigration debates in America today. He says that the plight of industrious immigrant families, documented or otherwise, ought to trigger empathy at the very least. Rather, he argues that it is usually met with “gleeful cheers” from repressive sections of society.
Even as Guy deals with these very real threats to his existence, he has kept his charm, humor, and sharp wit. In response to those who would threaten him, he quipped, “I think I can outrun you in these clothes.” This mix of levity and sincerity strikes the right chord with his fans and has been a big factor in his meteoric ascent.