16. Ad Rock
Height of Style: Licensed to Ill
Signature Look: Ska-influenced fedora and suit
Ad Rock's loose, organic style predated the modern-day hipster by decades. First it was frayed trucker hats and other ballcaps worn slightly askew, and then he switched it up to a ska-style suit with fly fedoraâ€”a look hardly any other guy has been unable to rock as successfully. His unmade look is now common amongst trendy Brooklynites and pretty much any kid who's ever listened to "(You Gotta) Fight For Your Right (To Party)." In other words, pretty much everybody.