There are few older men who can wear Supreme gear without looking like a total kook. Glenn O'Brien is one of them. GQ's resident style guy started out in New York's burgeoning music and arts scene, picking up sartorial influences from guys like Andy Warhol, Jean-Michel Basquiat, and Simon Doonan. What makes Glenn O'Brien look undeniably cool is his ability to throw on clothes and look like he immediately forgot what he's wearing. We'd kill for that amount of sangfroid.