Film: The Departed
Year: 2006
Signature Look: Hard-Boiled Boston Cop

South Boston cop Billy Costigan dresses like he's from Boston-tough as hell, and with a Red Sox cap. His loose-fitting workwear make him look like a low-level thug, which works well with his undercover steez, but he gets extra points for that black washed Levi's Trucker Jacket and the hardy leather Belstaff coat he layers over a hoodie in one of the film's pivotal scenes. He's not your typical action hero, he's dressed like the anti-James Bond-not suave, but pragmatic and ready to get his hands dirty.