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10. Cara Delevingne

10. Cara Delevingne

Dresses Like: A '90s skater
Occupation: Model

For how pretty she is, Cara dresses like a guy more than you think. Her menswear look is influenced by street and skateboarding, and often consists of varsity jackets, beanies, graphic tees, and sneakers. Everything about her casual style says she's easy-going and laid-back—the kind of chick ideal for cuffing season.

Tags: women-in-menswear
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