Band: The Rolling Stones; Keith Richards; The X-Pensive Winos

One of the best guitarists of all time was also a serious style pioneer. His penchant for wild-looking clothes with an edge combined the mod penchant for color with a rocker attitude. This is the guy that wore headbands eons before any '80s hairband thought to. His natural swagger and iconic style also provided the inspiration for Pirates of The Caribbean anti-hero Jack Sparrow, so much so that he signed on to play Sparrow's father, Captain Teague, in the film's sequels.