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.

ORLANDO BLOOM

The Lord of the Rings star picks a leather jacket and fancy white driving moccasins to accessorize his oversized shirt, distressed jeans and striking eye makeup at the Cirque du Soleil in Las Vegas.