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.

01 of 08

JUSTIN TIMBERLAKE

JUSTIN TIMBERLAKE
Billy Farrell/PMc/Sipa

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.

02 of 08

Ashton Kutcher

Ashton Kutcher
George Pimentel/WireImage

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.

03 of 08

ADAM BRODY

ADAM BRODY
Lisa Rose/jpistudios.com

The O.C. star pairs an iridescent button-down shirt and black dress pants with everyday Chuck Taylors and an olive knit cap for an appearance at the Starsky amp Hutch premiere in L.A.

04 of 08

ORLANDO BLOOM

ORLANDO BLOOM
Doug Benc/Getty

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.

05 of 08

LEONARDO DICAPRIO

LEONARDO DICAPRIO
Mario Anzuoni/Splash News

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.

06 of 08

JAKE GYLLENHAAL

JAKE GYLLENHAAL
Jill Johnson/jpistudios.com

An unshaven Gyllenhaal, star of the upcoming Proof with Gwyneth Paltrow, mixes black jeans, a T-shirt and boots with a blazer at the Independent Spirit Awards.

07 of 08

Heath Ledger

Heath Ledger
BIG Australia/BEImages

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.

08 of 08

COLIN FARRELL

COLIN FARRELL
Dave Benett/Alpha/Globe

The Dublin native – blond for his role in the upcoming Oliver Stone epic Alexander – tops his baggy jeans and well-worn shoes with a spiffy black oxford and pinstriped suit jacket at the London premiere of Intermission.

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