Dresses like: Jon Bon Jovi in the Fresh Prince's closet
Popular song: "Freedom! '90"Born in London, George Michael has had plenty of R&B hits and style to earn him a spot on this list. After wearing slogan T-shirts and bright neon colors during his Wham! Days, the "Father Figure" singer found a signature look that involved leather jackets, ripped jeans, and some aviator shades. However he didn't abandon his taste for flamboyant clothing. The singer sometimes rocked over-the-top colors like cobalt blue sweaters or orange suits that would make any Pitti Uomo attendee turn their head.