Star Men of Style

"He's bringing a whole new level of style to the world" with his "bling outfits," says PEOPLE style director Susan Kaufman of Grammy-winning Usher. And the singer (from left: in Los Angeles in October; at the MTV Video Music Awards in August; at a fashion event in New York last month) makes the most of his ensembles by accessorizing with a debonair pocket square or sunglasses.

The Finding Neverland star is a fashion maverick, says Kaufman. Depp (from left: at the 2004 Golden Globes; at the Venice Film Festival in September; at Neverland's London premiere in October) "goes out of his way to shake up the red carpet" with his fearless looks. "He'll channel Charlie Chaplin or Harry Potter."

Law's taste in clothes "are almost a throwback to the '60s-boy look – he's definitely a mod man," says Kaufman of the Alfie star (from left: at an L.A. premiere in September; in Manhattan in September; at the New York premiere of Alfie in October). "Here's a guy you're never going to see with Reebok running shoes with baggy jeans."

The O.C.'s Brody "is that cute guy on the street. You could see him carrying a skateboard," says Kaufman. "He mixes his neo-prep look" with an indie-rocker vibe. One style constant: Brody (from left: in L.A. in October; at a FOX event in Hollywood last month; at L.A. premiere in June) loves to wear sneakers.

The Newlyweds star (from left: at the VH1 Divas event in Las Vegas in April; at an L.A. club in October; at an American Music Awards nomination ceremony in September) "has such a clean-cut look. He's the all-American guy," says Kaufman. "He dresses in a way that every guy can relate to and dress like."

"He really has fun with clothes," says Kaufman of Kutcher, who'll wear a designer suit (left, at a Beverly Hills fashion event in March) or a kilt (center, dining out in Beverly Hills in September). "He's one of the chameleons of male fashion." And the former model (right, in L.A. in June) has "the confidence to carry it off."

Kaufman considers the Troy star a "young bohemian" when it comes to style. Bloom (from left: at the Pirates of the Caribbean premiere at Disneyland in 2003; in L.A. on Nov. 4; at the Cannes Film Festival in May) is "not afraid to wear jewelry and facial hair. He's a swashbuckling kind of guy."

"Subtly sexy" is how Kaufman describes singer-actor Marc Anthony's taste. "You'll never see him scruffy – he's always well put-together. He'll go out the door camera-ready." Yet Jennifer Lopez's husband (from left: in Manhattan in September; at the MTV Video Music Awards in August; at a Marc Jacobs show in New York in September) always manages to look "relaxed."

The Collateral star "favors simple cuts and streamlined suits," says Kaufman. "He knows what works best for him," including his "perennial favorite": leather jackets. The actor (from left: at a UCLA event in October; at the Mexico City premiere of Collateral and in Madrid, both in August) likes "solid-colored ties or a solid-colored shirt mixed with something simple."

"He's incredibly aware of his look and he mixes it up," says Kaufman of Kravitz (from left: at the Teen Choice Awards in August, at a London movie premiere in July; at the Latin MTV Video Music Awards in October). "He goes the full rock-star sexy guy route." Kravitz's must-have accessory of the moment: his wraparound Bottega Veneta sunglasses.

Though the Alexander star (left, in London in 2003; center, in Hollywood in June) might seem like he's saying, "'I don't care about clothes,' " says Kaufman, "he wants to look like a bad boy. He exudes cool." One of Farrell's classic looks (right, in Rome in 2003): "A sexy tight tee and jaunty jacket mixed with beaten-up jeans."

Rapper Andre 3000's "playfulness with clothes" helps him "go the distance with whatever look he's picking for that moment," says Kaufman. The OutKast frontman (from left: at a Bel Air charity event in April; in Beverly Hills in May; shopping on Rodeo Drive in March) has been sporting a "Southern gentleman" look lately, but his ever-changing look is like a "performance-art fashion piece."

"Nobody wears a tux as well as Pierce Brosnan," says Kaufman of the debonair After the Sunset star (from left: at a Dublin awards show in October; in New York City on Nov. 8; in Beverly Hills in October). "He's a grown-up, he's a man. There's nothing funky or trendy about Pierce. He exudes sophistication and class."

The multi-platinum-selling singer (from left: at the MTV Europe Music Awards in 2003; in L.A. in February and September) is a fan of layering clothes and has "a very casual, easy look," says Kaufman. One of Timberlake's signatures: hats. "He has fun with hats – he likes to wear knit caps and fedoras."

The Ocean's Twelve star "really appreciates well-tailored, well-fitting designer-level clothes. Anything he puts on is going to be incredibly chic and he has the body to wear it," says Kaufman. Pitt (from left: at the New York premiere of Troy in May; in Beverly Hills in September; on MTV's TRL in May) "is very aware of fashion."