Celebrity Style Smackdown. Who Wore It Best?

September 24, 2008 • Celebrity Style

This Smackdown is a battle of styling proportions. No one looks totally terrible, no one’s clothes are completely misfitting (except Ashanti…), and no one chose something incredibly innapropriate for their age. Instead, the decisions on how to wear the look made the winners and losers this time around. See the winning looks below!

Anne Hathaway vs. Carla Gugino in Jasmine di Milo


Winner: Gotta love the bold look of that dress on Anne, with those legs! We like Carla’s t-straps, but the belt is all wrong.

Shannen Doherty vs. Lauren Conrad in Richard Ruiz


Winner: In a surprise move for SCS, we’re taking LC! The color she chose, fit and styling are better on her, and we like Lauren in something a little more rock’n’roll and outside of her usual look. And we definitely don’t promote tanorexia, but Shannen could use some color in that color.

Eva Longoria Parker vs. Ashanti in Marchesa


Winner: Eva by a long shot. Ashanti needs to learn to go up a size. In everything. Fit over size, girl!

Hilary Swank vs. Ashley Tisdale in Jill Stuart


Winner: Both! Hilary wears this dress right for her age group- with classic sandals, jewelry and hair, and a pristine fit. Younger Ashley funks it up with some cool Mary Janes and more relaxed styling. Although really Ashley, we’d love you to do something other than this dirty hippie crimp to your hair. 

Jessica Simpson vs. Kelly Osbourne in D&G


Winner: Definitely a style step forward for newly successful country singer Jessica (no cowboy boots! wow!), but this look goes so much better with Kelly’s aesthetic. Her sleek hair and satin shoes complete the black and plaid look perfectly. The young Osbourne has been on fire since Fashion Week!

Heidi Klum vs. Jennifer Lopez in Roland Mouret


Winner: Heidi. Mainly because J. Lo pulled that BS "foot injury" excuse to get out of judging Project Runway, but also because we like Heidi’s vintage-inspired look over Jennifer’s simple styling.

Maria Menounos vs. Tori Spelling in Shoshanna


Winner: Honestly, we think that color could make anyone look busted. But we suppose it looks better on Maria? Hard to tell, since we’re blinded by that ridiculous 1960s green.

See, styling can make or break a good dress! Gotta think about those decisions, ladies!

Photos: People.com

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