19. Cee Lo Green
No matter what anyone thinks of how Cee-Lo dresses, it's clear that he doesn't care either way. Whether he's rocking full-on muumuus or one of his many, many motorcycle jackets, his style is simply fearless. However, it's important to note that it isn't always ostentatious. Even though he has a flair for dressing weird and loud, every now and then he can tone it down.