20. Big Gipp
Although his solo career may not have gone as swimmingly as Goodie Mob mate Cee-Lo, style-wise, he can stand toe to toe. Big Gipp isn't afraid to get weird with his style—but he keeps it cemented in the real world. Case in point: the cheetah shawl he wore over a suit at 2013's amFAR Gala. Or the crazy paisley jacket he wore at 2009's BMI Urban Awards. Considering Cee-Lo opted for a glittery motorcycle jacket, it's safe to say he held his own.