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.

Ashton Kutcher

Teaming distressed blue jeans, a casual crewneck and a striped ski hat with a luxe bomber jacket, Demi's leading man (with a mustache!) heads into the NBA All-Star game in L.A.