PEOPLE's Style Awards

Our style director, Susan Kaufman, reveals the stars who most deserve a fall fashion trophy. By Serena Kappes

01 of 12

BEST MATCHED COUPLE: JENNIFER ANISTON & BRAD PITT

BEST MATCHED COUPLE: JENNIFER ANISTON & BRAD PITT
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Whatever the occasion, Aniston (wearing Atelier Versace) and Pitt (in a Neil Barrett tuxedo) always choose clothes that complement each other, says Kaufman. Pitt (next up in Ocean's Twelve) and Aniston (currently filming Otherwise Engaged with Kevin Costner) are "both just simply chic. They're classic without being boring." Simply put, their outfits "are a backdrop for them as opposed to overwhelming them."

02 of 12

BEST STYLE AFTER BABY: GWYNETH PALTROW

BEST STYLE AFTER BABY: GWYNETH PALTROW
Chris Delmas/VISUALPress; Eliot Press/Bauer-Griffin

Forget dowdy sweats. Even though she's a new mom with a 4-month-old girl, Paltrow proves that "just because you've been pregnant doesn't mean you lose your sense of style," says Kaufman. The Sky Captain and the World of Tomorrow star looked fabulous during her pregnancy (left, in Stella McCartney) and has bounced back with impeccable post-baby fashions (right, in a chic cocktail dress). "We just give her kudos."

03 of 12

MOST DAPPER DUDE: USHER

MOST DAPPER DUDE: USHER
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"Usher is a throwback to the era of Frank Sinatra and the Rat Pack," says Kaufman. "It's that cool, laid-back school of dressing." The multiplatinum-selling Confessions singer knows how to work a suit – and look utterly "pulled together," from his pinky ring to his pocket square.

04 of 12

MOST OUTRAGEOUS: PARIS HILTON

MOST OUTRAGEOUS: PARIS HILTON
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The Simple Life star "is the girlie-girl every little girl wants to dress up as because she likes the glitz," says Kaufman. Whether it's wearing a jeweled dress (left, in Roberto Cavalli) or modeling her platinum-blonde locks, "everything about her is larger than life. When she walks in a room, everyone's going to notice her."

05 of 12

BEST USE OF TRENDS: LINDSAY LOHAN

BEST USE OF TRENDS: LINDSAY LOHAN
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At 18, Lohan is the perfect age for "going crazy with trends," says Kaufman. The Mean Girls star is the poster child for looking fresh in up-to-the-minute styles (left, in a vintage rock T-shirt and cut-off denim miniskirt). "Whatever the hippest, latest jean is, she'll be in it. Whatever the funky, cool new bag is, she'll have it."

06 of 12

MOST IMPROVED FEMALE: CHRISTINA AGUILERA

MOST IMPROVED FEMALE: CHRISTINA AGUILERA
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From "Dirrty" to divine, Aguilera has undergone a swan-like style transformation. "She was showing a little too much skin," says Kaufman of the singer (left, who'll be featured in the animated film A Shark Tale). A change in haircolor from dark to light, and a look that channels Marilyn Monroe (right, in a dress she designed with stylist Gitte Meldgaard), has given the singer a "classier" new appeal.

07 of 12

MOST IMPROVED MALE: LENNY KRAVITZ

MOST IMPROVED MALE: LENNY KRAVITZ
Richard C. Murray/LFI; Albert L. Ortega/Fashion Wire Daily

With his long and straightened hair, Kravitz (left) "really, really went wrong," says Kaufman. "He looked like a lady who lunched." But when he went back to basics in a natural new do (right), the rocker (who's been hitting talk shows in support of his album Baptism) regained his place in the pantheon of sexy musicians.

08 of 12

SINGULAR SENSE OF STYLE (FEMALE): GWEN STEFANI

SINGULAR SENSE OF STYLE (FEMALE): GWEN STEFANI
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"From the moment she burst on the scene with No Doubt, Stefani was setting her own trends," says Kaufman of the singer (left, in Louis Vuitton). Always sartorially adventurous, Stefani (whose solo debut album hits stores in November) "can carry something off that would look ridiculous on somebody else." The singer's own fashion line, L.A.M.B., showcases her love for fun streetwear.

09 of 12

SINGULAR SENSE OF STYLE (MALE): ANDRE 3000

SINGULAR SENSE OF STYLE (MALE): ANDRE 3000
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A fashion chameleon, the OutKast frontman can go from '60s-looking Jimi Hendrix-esque garb to funky prepster wear (left) and still be true to his daring sense of style. "He loves to switch it up and shock people," says Kaufman of the MTV Video Music Award-winning rapper. The secret to his appeal? "Confidence. That's the most important thing."

10 of 12

BEST RED CARPET: CHARLIZE THERON

BEST RED CARPET: CHARLIZE THERON
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Hands down, the Head in the Clouds star is the "queen of the red carpet" this year, says Kaufman. "She dressed spectacularly for every event. She knows how to work it." The statuesque Oscar winner (left, in Dior by John Galliano) pays attention to every element of her look: Her "hair, makeup and jewelry are never overdone."

11 of 12

MOST ACCESSORIZED: JESSICA SIMPSON

MOST ACCESSORIZED: JESSICA SIMPSON
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"This is a girl who loves, loves, loves her bags, her shoes, her sunglasses, her headscarves," says Kaufman of the Newlyweds star. Whether it's glamorous incognito movie star (left) or a bohemian look, Simpson's penchant for finding the right accessories completes it. "You know she just has a great time shopping."

12 of 12

BIGGEST BOMBSHELL: BEYONCé

BIGGEST BOMBSHELL: BEYONCé

Beyoncé (left, in Dolce amp Gabbana) isn't afraid to highlight her curves. She's got "the body to die for – and she dresses to show it off," says Kaufman. Yet the singer (who'll return with a new Destiny's Child album in November) has a timeless beauty. "You could put her in the '40s and she'd still be a woman of the moment."

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