29. Paulie Shore
Why He Made The Cut: Style isn't that serious, buuuuudddy.
The laid-back SoCal style was perfectly embodied by Paulie Shore. Besides his penchant for wrapping up his curly locks in a headband, almost everything he had was sleeveless. Whether they were vests or cut-off jean jackets, this was a dude who seriously loved to let his arms breathe. Always the stoner buddy in films like Encino Man, his own film career made him a leading man without compromising his eccentric style.