35. Charlie Sheen
On a list rife with repeat bowling-shirt offenders, there is no question of who the undisputed king is. The man literally created a primetime sitcom character based on an outfit composed of gross shirts, khaki cargo shorts, and Merrells with socks. But what might be worse is that he literally wears it off the set and throws on a flame-ribbon fedora for an cohesive day-to-night appeal. #FAILING.