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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LEONARDO DICAPRIO

At a Beverly Hills benefit, the star of the upcoming Aviator (with Cate Blanchett and Gwen Stefani) makes an entrance in baggy blue jeans, sneakers and a sporty baseball cap, dressed up with a neat charcoal jacket and blue oxford.