14. Big Sean
It isn't that Big Sean just became stylish now—the opposite, he's been one of the better dressed dudes in the industry for years. He nabs a spot on this list because of his new-found minimalistic, sometimes street goth look. He's worn more familiar designer brands, such as Balenciaga and Balmain in the past (and still does at times). But he's widened his reach, adding lesser known label such as Alexandre Plokhov.