Not only one of the most stylish rappers ever, 3 Stacks is definitely Atlanta's most stylish son. The secret to his style is his ability to transcend boundaries—streetwear, prep, high fashion, workwear—there seems to be no style he's afraid of.  Long before Kanye West got weird with masks or had put on his first Dior suit, Andre 3000 was making the case for rappers in skirts and slim-cut suits.Most notably, Andre 3000 paved the way for every rapper who wanted to dress against the grain.

He had his fair share of criticism from the media (like the Native American outfits at the 2004 Grammys) and ribbing from his friends (just peep the first few seconds of the music video to "International Players Anthem"), and he doesn't let any of it get to him. The best part? He embraces his style mistakes. But even then, a misstep for Andre 3000 is like a step up for the average rapper anyway.