Jack Twist (Jake Gyllenhaal) in The 25 Most Stylish Law-Breakers list

9. The Joker (Heath Ledger), The Dark Knight

Looking deranged takes no skill. Looking deranged and stylish takes genius. You match your hair to your three-piece suit—your green and purple suit, the one with odd geometric patterns and a sick trim fit. And to edge ahead of the other peacocks strutting their stuff in Gotham, you add a lot carefully smudged make-up. It's the perfect touch of crazy for the Why-So-Serious icon.—A.R.

19. Jack Twist (Jake Gyllenhaal), Brokeback Mountain

It's Montana in 1963. Shacking up with another cowboy won't be legal for another 34 years. It takes guts, to say the least. In shearling jackets, properly-matched denim, and, of course, a Western hat, Jack Twist dresses the part of a rugged fella willing to break all sorts of social and literal laws. The real style is in the way Twist pulls his clothes on though—consciously. Even self-consciously. His insecurities come out in the way he bundles his hands in pockets and lowers his hat's brim. He makes those tics look covetable though, even if his situation isn't.—A.R. Source: www.gq.com