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.

JUSTIN TIMBERLAKE

Outside a Vanity Fair party in L.A., the bearded solo artist is an exercise in contrasts. He shows his casual side with jeans, sneakers and a logo sweater, but his shirt, though untucked, adds a splash of stylish color, and he tops it all off with a sharp blazer.