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.

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Heath Ledger

At the Australian premiere of 21 Grams (which stars his girlfriend, Oscar nominee Naomi Watts), Ledger lightens up a businesslike pinstriped suit with an untucked shirt, shades and scuffed shoes.