Star Guys: Shabby or Chic?

For years, Hollywood's leading ladies have been mixing high-end designer clothes with casual pieces – and now the guys are getting into the act, pairing dressy jackets and pants with scuffed shoes and logo tees. Take Justin Timberlake, who favors everything from Abercrombie & Fitch to Roberto Cavalli. Check out the looks on fellow It guys, including Jake Gyllenhaal and Leonardo DiCaprio.

JAKE GYLLENHAAL

An unshaven Gyllenhaal, star of the upcoming Proof with Gwyneth Paltrow, mixes black jeans, a T-shirt and boots with a blazer at the Independent Spirit Awards.