In the '90s, self-proclaimed feminist Kurt Cobain wore Courtney Love’s dresses on stage. Then Marc Jacobs took a shine to the skirt-and-button-up combo. And recently, Seth Meyers took the stage at the CFDAs in Comme des Garcons.
So, we have to ask — why not? Avant garde, unconventional, or just plain weird, we're celebrating the men who haven't shied away from a shorter hemline. Will we be running out to buy our boyfriend or grandpa a midi number anytime soon? Honestly, probably not. But with so many influential fellas paving the skirted road, we find it hard not to take a few cues from these trailblazers. After all, if we can praise Annie Hall for rocking menswear like a boss, then shouldn't we be just as excited when the tables are turned?
Click through for a look back at some fashionably fearless men. And don't skirt the issue; take to the comments and tell us where you stand!