6. Gucci Mane
Despite what you might think of his outlandish tattoos, Gucci's style hovers in that sweet spot between actually good and so crazy that it works. The big belly, ice cream cone chain, and undeniable attitude that screams "I just don't give a fuck" is really what makes Gucci Mane stylish. That he decides to wear Versace scarves around his head or designer sunglasses is merely the icing on the cake.