Leonardo DiCaprio's Most Stylish Roles

16. Josh

Film: Critters 3
Year: 1991
Signature Look: Wavy T-shirts

DiCaprio's first role made him an instant style icon. Just look at those amazing T-shirts! If they came out today from a streetwear brand, we'd line up for them. Plus he really knows how to accessorize: with a Game Boy, duh.

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