Let me just set the record straight on this: If there’s anything that GQ’s current crop of Best New Menswear Designers in America proves, it’s not that menswear is harder to define than ever, it's that it's always been like that. Even in the rapidly growing world of men's clothes and the people that nerd out about it, plus ça change, plus c'est la même chose.
To put things in perspective, the BNMDA program has been around since 2008, and the first winner was Daiki Suzuki of Engineered Garments, followed by Robert Geller in 2009. Both designers' visions for men's clothing couldn't be any more different, but both were deemed worthy of $50,000 and a Levi's collaboration. The upscale take on sweatpants and athletic gear? You can pin that on 2011 winner Alexander Wang (a somewhat controversial choice at the time), who had guys coveting expensive elasticated trousers and pieced leather jackets long before En Noir or John Elliott.
Even in the fledgling days of #menswear blogging, there were pre-existing, distinct internet style tribes, ranging from the iGents who frequent Ask Andy About Clothes, the recovering hypebeasts/early trend adopters on SuperFuture, and the high-fashion refugees who banded together to form StyleZeitgeist. At best, GQ functions as a good barometer of American men's style—it's not where young brands get discovered, but a place where they have the opportunity to go mainstream. Nothing says, "We're coming for you, Middle America" quite like a co-branded collaboration with the Gap. It's a big retailer that literally addresses the taste disparity between these brands and its average customer in its name.
So no, "this crazy thing called 'menswear'" is not headed in any particular direction, because, in general, "menswear" simply refers to the clothes. The guys who want to kill it in the office (i.e. anyone with a regular 9-5) will continue buying suits. The bro who is the designated "stylish" one in his group of douchebags will continue to wear the hell out of Saturdays. And the goth ninjas will continue looking for new ways to layer long shirts under and over jackets made from exotic animal skins. Even the guy who is not into fashion, but "just wants to look good in clothes," will keep buying brands like J. Crew, Club Monaco and, yes, the Gap.
However, if you want to address which designers and aesthetics have really influenced how men dress, and really take a closer look at the evolution of men's clothing in the past few years, well that, mon frère, is called "fashion." And that's a word men have only just begun to embrace.