1 of 19 John Shearer/WireImage.com
HitGrey's Anatomy star Chandra Wilson looks vibrant, sassy and youthful in this bold, orange gown. The actress makes us feel like summer is here four months early as she arrives at the 40th NAACP Image Awards at L.A.'s Shrine Auditorium.
2 of 19 John Shearer/WireImage.com
HitMusician Seal, aka Mr. Heidi Klum, arrives at the NAACP Image Awards looking dapper and ready to impress. But where's the missus? She might be your most reliable fashionable accessory — although that tie is super hot.
3 of 19 John Shearer/WireImage.com
HitActress Sanaa Lathan arrives at the NAACP Image Awards in a va-va-voom, low-cut red gown that could stop traffic.
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MissWe're trying to find one nice thing about Keshia Knight Pulliam's outfit... nope, can't do it. The House of Payne star arrives at the NAACP Image Awards in a cobalt-blue prom dress circa 1993. With the piled-up hair and crystal embellishment, we're wondering where she's stashed her white limo and carnation corsage?
5 of 19 John Shearer/WireImage.com
HitActress and recent Saturday Night Live host Rosario Dawson looks phenomenal in a vintage-style, strapless black cocktail gown. Though the jury is out on her hairstyle, Dawson's dress is classic and elegant as she strikes a pose at the NAACP Image Awards.
6 of 19 Duffy-Marie Arnoult/WireImage.com
MissThe Closer's Kyra Sedgwick and husband Kevin Bacon should technically be a hit, but they just miss the mark at the premiere of Kevin's Taking Chance. Upon a second look, we had to ask why he's wearing a velvet blazer with black jeans? Plus, his hair is as unbecoming as his expression. And Kyra, why would you pair such a short, bright dress with the most unsexy boots in the universe?
7 of 19 Jamie McCarthy/WireImage.com
Miss30 Rock's Jane Krakowski would be a mega hit at the 6th Annual Woman's Day Red Dress Awards in New York City if she had just worn a red dress like all the other ladies. Her hair is beautiful and she has a rockin' body, so why did she shrink-wrap an American flag made of Campbell soup images on herself?
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MissWe wonder if singer Solange Knowles is feeling as drafty as she looks wearing this super-short red dress for the Sixth Annual Woman's Day Red Dress Awards. The design totally reminds us of a red, hard candy sucker from our grandparents' house.
9 of 19 Mark Von Holden/WireImage.com
HitGossip Girl's Taylor Momsen poses at a screening of Two Lovers. The actress — who usually sports heavy raccoon-eye makeup — looks fun and modern in this sleeveless black mini. She also works some sexy bright-pink, peep-toe heels to make her outfit pop.
10 of 19 Anita Bugge/WireImage.com
ER's Angela Bassett stuns in this platinum, one-shoulder gown at the Berlin Film Festival premiere for Notorious. We would like to know what Angela's secret is for looking so gorgeous and youthful on and off the red carpet.
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HitThough we don't want to know what the combined cost is of all the highlights, tooth-whitening and spray-tanning going on in this picture, Kellie Pickler, Julianne Hough and LeAnn Rimes all look fabulous at the Academy of Country Music Awards nominations announcement.
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MissYikes! What are these two — who usually light up a red carpet — wearing at the Unforgettable Evening benefit? Rita Wilson's turquoise, strapless dress looks frumpy, like an expensive potato sack. We hope Sheryl Crow is going for some ribs later with that bib of a dress she's wearing.
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MissWe'd like to know when Gwyneth Paltrow transformed from a fashionista to an 80-year-old, Upper East Side socialite? She looks gaunt, washed out and way beyond her years in this cream getup.
14 of 19 Michael Gottschalk/AFP/Getty Images
MissKeira Knightley looks ridiculous in this boxy, unflattering pantsuit as she poses on the red carpet for the premiere of Cheri at the Berlinale Film Festival. Plus: how about getting rid of the bangs so we can actually see your face?
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Sorta HitThough it pains us to give this permanently boho-chic chick a passing grade, this outfit definitely works for Sienna Miller. Which is a good thing considering she just won the Elle Style Icon Award. The frock fits her frame, has a splash of spring color that pops from the black ensemble and she looks happy. It's refreshing to not see the sucked-in cheek scowl (Keira!).
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MissIt's official: Courtney Love morphing into (a plastic) Madonna. In fact, at first glace, we thought this was Madonna on a bad night. The singer (where has she been, anyway?) made us shake our heads by donning this tragically ugly black gown at the Elle Style Awards.
17 of 19 Jon Furniss/WireImage.com
MissWhat a hot mess this pair is! A rumpled and sloppy-looking Mickey Rourke poses with Thandie Newton — and her hideous dress of many colors — at the Elle Style Awards.
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MissOh, how we miss Chuck from Pushing Daisies! Anna Friel, who usually dazzles on the red carpet, should have taken a cue from her character's style at the Elle Awards. This dress is dumpy and lumpy, while the pattern is just ugly. Better luck next time!
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HitDebra Messing may be feeling a little sorry for herself now that her latest show, The Starter Wife, has just been cancelled. But looking good is the best revenge! Messing is sleek and polished in this funky little belted dress at the Love benefit to support WET's (Women's Expressive Theater) 10th season. Love the hair and the asymmetrical hemline, too!