2. Michael Jackson
There is no denying that The King of Pop had some of the best style of our time. As a youngster he was at the forefront of stylish dudes, but when he hit his stride in the '80s he was powerful enough to even make glittery shit cool. He may have strayed into very strange territory later in life, but when MJ ruled the world, his steez was definitely a big part of his monumental success.