PEOPLE Style Awards

Angelina, Beyonce, Jessica – style director Susan Kaufman reveals her annual list of fashion's biggest stars. By Serena Kappes

01 of 13

SEXIEST RED-CARPET MOMENT: ANGELINA JOLIE

SEXIEST RED-CARPET MOMENT: ANGELINA JOLIE
tsuni/gamma; Bill Davila/startraks

Angelina Jolie turned heads when she showed up to the June 7 Hollywood premiere of Mr. amp Mrs. Smith in a sultry Versace leather gown. "Who else could wear black leather head to toe and look sexy and not trashy?" says Kaufman.

02 of 13

BEST ACCESSORIES: BEYONCé

BEST ACCESSORIES: BEYONCé
Lawrence Schwartzwald/Splash News; Theo Wargo/WireImage

"Beyoncé plays up her diva-ness with her accessories," says Kaufman. With a head-scarf, chandelier earrings and her favorite Bracher Emden multicolored bag, the Destiny's Child singer rocks a boho-chic look in New York City (left). And at MTV's Video Music Awards she pairs a Dolce amp Gabbana dress with oversized Lorraine Schwartz donut earrings and chunky bangles. "And she doesn't look overdone," says Kaufman.

03 of 13

WORST-DRESSED COUPLE: PARIS & PARIS

WORST-DRESSED COUPLE: PARIS & PARIS
BAUER-GRIFFIN (2)

"They've reached the level of almost being cartoon characters," says Kaufman of Paris Hilton and fiancé Paris Latsis's style (left, in L.A.; right, in Monaco). "Put them together and it's a smorgasbord of crazy mixes of print and pattern." Yet no matter how badly dressed the couple are, all eyes are on them. "It's double the pleasure of bad fun," says Kaufman.

04 of 13

BEST PREGNANCY STYLE: HEIDI KLUM

BEST PREGNANCY STYLE: HEIDI KLUM
London Entertainment/Splash News; Evan Agostini/Getty

Supermodel Heidi Klum embraced the beauty of maternity. "She's not afraid to show her shape," says Kaufman. Whether in New York City in an empire-waisted top and jeans (left) or in a slinky Donna Karan gown at the CFDA Fashion Awards (right), Klum "exults in her pregnancy."

05 of 13

SINGULAR SENSE OF STYLE (MALE): JOHNNY DEPP

SINGULAR SENSE OF STYLE (MALE): JOHNNY DEPP
Kevin Winter/Getty; tsuni/gamma

Forget designers of the moment – for Johnny Depp, it's vintage all the way, from a natty fedora down to spats (left, at the Golden Globes; right, at the L.A. premiere of Charlie and the Chocolate Factory). "He's his own guy," says Kaufman. "He bucks all of typical Hollywood male dressing."

06 of 13

MOST IMPROVED FEMALE: ASHLEE SIMPSON

MOST IMPROVED FEMALE: ASHLEE SIMPSON
Kevin Mazur/WireImage; Lisa O'Connor/ZUMA

About to turn 21, "Ashlee Simpson is shedding her kitschy rock-girl look with the jet-black hair, funky accessories and '80s feeling and is wearing elegant clothes," says Kaufman. Her teenybopper image (left, in 2004) has been replaced by a more mature look (right, in Giambattista Valli at the MTV VMAs). "She's coming into her own as a woman."

07 of 13

WORST FASHION MAKEOVER: JENNIFER LOPEZ

WORST FASHION MAKEOVER: JENNIFER LOPEZ
David Edwards/Dailyceleb; Jun Sato/WireImage

In 2004, Jennifer Lopez looked "sexy, glamorous and put-together," says Kaufman of the singer-actress (left, in J. Mendel). But in 2005, she has had some major slip-ups. Her "fraulein" look (right, in Tokyo) stands out. "It's a combination of the Heidi hair, the big baggy dress, the slouchy boots," says Kaufman. "It's a fashion disaster."

08 of 13

TRENDIEST BEST FRIENDS: LINDSAY LOHAN & NICOLE RICHIE

TRENDIEST BEST FRIENDS: LINDSAY LOHAN & NICOLE RICHIE
Mavrix Photo; X17

From chunky necklaces, big bags and oversized sunglasess to cowboy boots with dresses, pals Nicole Richie and Lindsay Lohan (in Beverly Hills) are always wearing "the hot new things," Kaufman says. "It's almost like playing dress-up with them."

09 of 13

MOST IMPROVED MALE: JACK OSBOURNE

MOST IMPROVED MALE: JACK OSBOURNE
Vince Flores/Celebrity Photo; DAVID FISHER/LFI

"Talk about extreme makeovers – Jack Osbourne has gone the full distance," says Kaufman. Ozzy's son has not only trimmed down, he's taken up his style a slew of notches. Once sloppy and grungy (left, in 2004), he's now tailored and funky (right, in London in June). "Kudos to him for the effort," says Kaufman.

10 of 13

BIGGEST TRENDSETTER: SIENNA MILLER

BIGGEST TRENDSETTER: SIENNA MILLER
Can Nguyen/Capital Pictures/GAMMA; BAUER-GRIFFIN

Sienna Miller "has that cool Brit-girl sense of style and mixes designer with vintage," says Kaufman of the budding fashion icon (left, in London; right, at a polo event in Berkshire). "Somehow she puts it all together and makes it work." The handbag company Kooba even named the highly popular Sienna bag after her. But her biggest fashion feat? "She single-handedly brought back the denim vest," says Kaufman.

11 of 13

BEST-MATCHED COUPLE:PENELOPE & MATTHEW

BEST-MATCHED COUPLE:PENELOPE & MATTHEW
LDP Images

Lovebirds Penelope Cruz and Matthew McConaughey "make an effort to look good together." Whether sporting breezy summer looks (left, in Madrid) or decked out in high-fashion at the Spanish premiere of Sahara (she, in custom-made Ralph Lauren; he, in a Dolce amp Gabbana suit) "they complement one another."

12 of 13

SINGULAR SENSE OF STYLE (FEMALE): GWEN STEFANI

SINGULAR SENSE OF STYLE (FEMALE): GWEN STEFANI
Jeff Vespa/WireImage; Luis Martinez/AFF-USA

"Gwen Stefani is a complete original," says Kaufman. "She always defies convention." Only the "Hollaback Girl" singer can pull off a plaid jacket, leather shorts and leggings (left, in Hollywood). And at the VMAs, she scored $50,000 from Diddy for being best-dressed in her '40s-inspired leopard halter dress from her L.A.M.B. collection (right). "She has such a sense of her own style and a conviction about it," says Kaufman.

13 of 13

BEST ALL-AMERICAN STYLE: JESSICA SIMPSON

BEST ALL-AMERICAN STYLE: JESSICA SIMPSON
John Smith/startraks; LUIS GUERRA//RAmey

Jessica Simpson makes an American fashion staple – jeans – seem glamorous (right, in New York City). "She has said she has hundreds of pairs," says Kaufman. And when she donned short-shorts (left), she resuscitated a fashion trend. "Now all the jeans manufacturers have come out with their Daisy Dukes," says Kaufman. "She's a real jeans girl."

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