Dresses Like: A British juvenile delinquent 
Occupation: Singer

One of the things the Bad Boy princess is known for is her half-shaved haircut—she had, and still has, every chick out there thinking she could pull it off. But let's not forget, her personal style has also influenced a number of women. It's sexy and hood at the same time. It's a mix of streetwear and designer labels. She dresses masculine without looking butch. And for that, we salute Cassie.