If you spend any time on Twitter, you probably know the handle @dieworkwear by heart. It belongs to Derek Guy, aka “the menswear guy” expert extraordinaire.
I have to confess that until I started writing this essay, I wasn’t even sure if Derek Guy was his real name. I hadn’t bothered to check because I trust him implicitly. Perhaps controversially, I enjoy nearly all his posts, so why wouldn’t I trust him?
He blends sartorial insights with pop cultural awareness, self-deprecation, and sarcasm. He covers topics like men’s suits (a staple), the now infamous “collar gap,” the “level of tailoring that’s very rare to see nowadays even on the wealthy,” his disdain for dress sneakers, young Harrison Ford in short shorts, and ample praise of the Polo Ralph Lauren bear — all part of a larger than life online persona.
Derek Guy has become a widely acquired taste, with Elon’s For-You-ificiation of Twitter playing a big role. Pre-Fall 2022, Guy had just tens of thousands of followers. His account gr…