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.

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.