8. Drama (Kevin Dillon); Entourage

Say what you will about Drama; he can't act and he's a co-dependent of his younger brother. Despite all of that, the man has style. To take it a step further, he's probably one of the most daring dressers to ever grace the Home Box Office. We wouldn't always go with some of his choices (the man loves his skin-tight Ed Hardy and Affliction tees) but more often than not, Drama put together some unpredictably fly wardrobe choices over the years. Victory, indeed.