27. Andre 3000 with the football pads in "Rosa Parks."
Back when being a total weirdo was a relatively frowned upon, 3 Stacks unapologetically let the world know that he absolutely was one with his wardrobe choices in "Rosa Parks." Most notable, however, was the set of football pads worn as outerwear. Yeah, the baseball catcher vest was wild, but when we think of Outkast being, well, outcasts, it's this visual that comes to mind.