8. Glenn O'Brien

Occupation: Writer

Glenn O'Brien is more than just "The Style Guy" at GQ, he's a New York institution. He literally rubbed shoulders with Basquiat during his "SAMO" days and pretty much did ratchet shit before "ratchet" was even a word. Case in point: his public-access TV show, "Glenn O'Brien's TV Party," which featured performances from acts like Klaus Nomi and Blondie. O'Brien isn't simply stylish, he never stopped being cool. Even though he's a veteran in the scene, he's still outdressing dudes more than half his age. Can you imagine any other dad wearing Supreme next to Tyler, The Creator and holding his own, style-wise? Yeah, didn't think so.