8. Amber Rose
Dresses Like: A barber shop regular
Occupation: Model, Singer
Amber is usually in tight mini dresses or equally tight leggings, but she also knows how to rock menswear-inspired looks, too. When she does, it involves sneakers, baggy pants, or good ol' Timberland boots. It's not easy to pull off something so masculine, so we respect her swag. Although, let's be honest, you could never really mistake her for a guy—from the front or back. She's has a beautiful face and, well, the assets to match.