Film: Titanic
Year: 1997
Signature Look: Ashy to Classy

It's no wonder that Jack Dawson is the crush of so many teenage girls. His style embodies how most women would want a man to dress: comfortable most of the time, but cleans up really well. His workwear-inspired, rough-around-the-edges style works for him, pulling off tab collar shirts and corduroy pants with ease, stuff you could easily find at a J. Crew store today. But his sudden transformation from intriguing bad boy to dapper gent really seals the deal. He's like the guy that knows everything about style, but doesn't want to go all-out unless he has to.