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2008's Best-Dressed

Published December 31, 2008 at 1:29 p.m.
Updated December 31, 2008 at 7:13 p.m.

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Actress Katherine Heigl arrives at the 80th Annual Academy Awards held at the Kodak Theatre on February 24, 2008 in Hollywood, California.

Photo by Vince Bucci/Getty Images

Actress Katherine Heigl arrives at the 80th Annual Academy Awards held at the Kodak Theatre on February 24, 2008 in Hollywood, California.

Singer Rihanna arrives at the 2008 BET Awards held at the Shrine Auditorium on June 24, 2008 in Los Angeles, California.

Photo by Frazer Harrison/Getty Images

Singer Rihanna arrives at the 2008 BET Awards held at the Shrine Auditorium on June 24, 2008 in Los Angeles, California.

2008's Best-Dressed

The Rocky's fashion expert Lesley Kennedy crowns these celebs the winners.

Normally, when we look back at the year in fashion, we highlight the most beautiful gowns spotted at red-carpet events. But, the thing is, remembering the really, really bad dresses is a whole lot more fun. You see, nobody is perfect. Sure, the Gwyneths, the Kates and the Keiras usually get it right. But, to our catty delight, even they are capable of getting it terribly wrong.

On this page, we've chosen seven stunners from 2008. Feel free to sigh and even feel a bit jealous as you check them out. Then flip to Spotlight 10 and 11 and join us in a round of "Oh, no, she didn't!" Here's to a 2009 filled with more fashion missteps. Happy New Year!

The Rocky's fashion expert Lesley Kennedy crowns these celebs the winners.

1. Katherine Heigl: Now, this is what a movie star should look like. In her red Escada Oscar gown, she was the epitome of classic beauty.

2. Sienna Miller: When you can make sheer look stunning, you know you've got it going on. It helps when the dress is Dior - and you weigh about five pounds. Still, Miller wowed the crowds at the BAFTA awards in February in London.

3. Gwyneth Paltrow: If we had those legs, we'd wear this sexy Balmain lace mini dress daily. She wore it to the Iron Man London premiere in April. Paired with the little tuxedo jacket? Oh, so chic.

4. Heidi Klum: It's hard not to look good when you're Heidi, but she was simply dazzling in this Armani Prive silver gown on Emmy's red carpet in September.

5. Michelle Obama: The Thakoon floral dress she wore for her husband's acceptance speech in Denver in August cemented her as a fashion icon on the rise.

6. Anne Hathaway: Smart, sophisticated and totally glam in strapless Marchesa at the Madrid premiere of Get Smart in July.

7. Rihanna: Yellow was a popular, albeit difficult, color to wear in 2008. But Rihanna rocked it, looking like a ray of sunshine in this Giambattista Valli gown she wore to the BET Awards in June.

Worst-dressed of 2008

1. Eva Longoria Parker; 2. Paris Hilton; 3. Sarah Silverman; 4. Kate Bosworth; 5. Mandy Moore; 6. Kate Perry; 7. Lucy Liu; 8. Jennifer Love Hewitt; 9. Katie Holmes; 10. Sarah Jessica Parker; 11. America Ferrera; 12. Kate Beckinsale; 13. Kelly Osbourne; 14. Heidi Montag; 15. Janet Jackson; 16. Fergie; 17. Keira Knightly; 18. Beyonce; 19. Jada Pinkett Smith; 20. Ashley Judd; 21. Kate Hudson; 22. Paula Abdul; 23. Blake Lively; 24. Scarlett Johansson; 25. Anna Wintour; 26. Melanie Brown; 27. Sigourney Weaver; 28. Kristin Chenoweth; 29. Mary-Kate Olsen; 30. Gwyneth Paltrow; 31. Thandie Newton; 32. Hillary Duff; 33. Ashanti; 34. Hayden Panettiere; 35. Naomi Campbell; 36. Andre Leon Talley. 37. Madonna

Worst. Trend. Ever.

A cute preppy headband is sweet. A headband worn on the forehead is just plain ick. And no one wore it more often than Mischa Barton. Let's hope this unsightly trend dies a quick death in 2009.

Comments

  • January 1, 2009

    11:08 a.m.

    Suggest removal

    JamesTaylorSucks writes:

    Leslie exposes her political bias by including Mrs. Obama. Please show us again the "Black Widow Dress". If you want a politician's wife, Cindy McCain will do nicely. Oops, she's Republican. Good luck with the job hunting come February!