3. Diddy

Whether you look at photos of classic Puff Daddy or present day Ciroc Boy, there's no denying that Diddy has an eye for flamboyant style. We rocked with all his trends from shiny suits to velour to bottom grills. Plus, it's pretty impressive that Sean Jean is still strong in the game 13 years since it's inception.

Click here to see Diddy's Style History.