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People reveals its best and worst-dressed of ’09

Kate Winslet, Michelle Obama, Reese Witherspoon, Taylor Swift and Nicole Richie are on the good side of People's Best & Worst Dressed List 2009. Among the fashion flubs that made the Worst list were Kate Gosselin's "reverse mullet" and Jessica Simpson's "mom jeans."
/ Source: TODAY contributor

Kate Winslet seems to have as many designer gowns as she has prestigious films, and she is now an official style icon as well as an Oscar-winning Best Actress: On Wednesday, People magazine named the British actress the best-dressed on the red carpet.

The 33-year-old Winslet joined the likes of Michelle Obama, Reese Witherspoon, Taylor Swift and Nicole Richie on People’s Best & Worst Dressed List, honoring the high and low ends of star style for 2009.

In unveiling the winners and losers exclusively on TODAY, People Style Editor Clarissa Cruz told Natalie Morales picking the best in a sea of stylish celebrities is no easy task.

“We looked at thousands of pictures in the course of the year,” Cruz said. “The one thing that the Top 10 had in common is that they just had a great sense of personal style and they were out and about, and had a great fashion year.”

Wearing out the red carpetBeing named best dressed on the red carpet is arguably the biggest honor, because that’s when celebs do their utmost to put their best fashion feet forward. Winslet in particular wore out her high heels this year, because her star turns in “The Reader” and “Revolutionary Road” put her front and center at all the major film awards shows.

“She just looked fantastic,” Cruz said of Winslet. “She was all over the awards circuit, and she got it right every time. She wore Narcisco Rodriguez, she wore Yves Saint Laurent, and she just looked appropriate and glamorous.”

First lady Michelle Obama, the only non-performer to make the Top 10, received the “Best Accessible Glamour” award, earning points for moving back and forth seamlessly between off-the-rack chain stores and hot designers. “She wears [designer] Jason Wu as well as J Crew, and that’s stuff that anyone can buy at the mall,” Cruz told Morales.

Witherspoon proved that great things — and great style — can come in small packages. Cruz said the 5-foot-2 actress won the “Best Short Dresses” nod for knowing exactly what looks good on her. “It’s important to get the hemlines just right when you’re petite,” she said. “She looked very modern, very confident; she worked the patterns. She looked great.”

Taylor Swift may not be at the top of Kanye West’s personal playlist, but she was tabbed for People’s “Best Sparkle” award. The twinkle in the country star’s eyes might only be matched by her love of all that glitters.

“She has so much fun with fashion,” Cruz said of People’s youngest best-dressed winner. “She told us she loves anything that glitters, and she chooses that for her red carpet outings all the time. It’s really fun and fresh.”

Wild child turned doting mom Nicole Richie had her second child by rocker Joel Madden, son Sparrow, on September 9, and she rocked a fresh maternity fashion looks throughout her pregnancy, Cruz said.

“It’s very bohemian, very hippie chic,” Cruz said of Richie, bestowed People’s “Best Maternity” award. “It just looked really great.”

Rounding out the Top 10 were Beyonce (Best Street Chic), Vanessa Hudgens (Best Hippie Chic), Freida Pinto (Best Use of Color), Cameron Diaz (Best Jeans) and Kim Kardashian (Best Bikinis). But not to be left out, TODAY’s own Kathie Lee Gifford also made the cut, being named to the “Chic at Every Age” list, along with the likes of Christie Brinkley and Jane Seymour.

Fashion flubs
Of course, what fun are fashion “do’s” without some fashion “don’ts?” People also let its snarkier side come out as it named some of the biggest fashion misadventures of the year.

Heading up that list is what sits on the head of “Jon and Kate Plus 8” reality TV star Kate Gosselin. Her gravity-defying ’do has become go-to fodder for comedians, and People couldn’t resist having its own poke at Gosselin’s tresses.

“It was a big hair ‘don’t,’ ” Cruz told Morales. “It was kind of a reverse mullet. Some people may have wanted to do it, but there’s the wig version in stores just in time for Halloween, so that will be pretty funny.”

Then there’s January 25 — a day that will live in fashion infamy. Performing at a Chili Cookoff festival in Pembroke Pines, Fla., singer/actress Jessica Simpson strutted on stage in a high-waisted nightmare pair of jeans that sent the blogosphere gasping for adjectives. It also earned her a spot on People’s Most Memorable/Shocking Moments list.

“They’re very unflattering,” Cruz said of the “mom jeans” Simpson sported that day. “Some people have a bad hair day. She had a very bad pants day. It just wasn’t the best look for her.”

People magazine’s Best & Worst Dressed 2009 issue, which also features best-dressed men such as Brad Pitt, Bradley Cooper and Robert Pattinson, hits newsstands Friday.