Reese Witherspoon's Best Looks of All Time

We celebrate the mom-to-be’s 36th birthday with a look back at her 20 most fashionable leading lady looks
By Catherine Dash
Updated March 21, 2012 10:00 AM

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THE MINIMALIST, 2000

Credit: Ron Galella, Ltd./Wireimage

hit her style stride at the 2000 Golden Globes (she earned a nod for her turn in Election), wearing a stylish-yet-safe black strapless gown, plus red lips and tousled hair.

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ON FIRE, 2004

Credit: Kevin Mazur/Wireimage

New do, new hue! At the N.Y.C. premiere of Vanity Fair, the actress stepped out of her comfort zone in a cherry-red Alberta Ferretti frock – but with a tea-length hem and cap sleeves, the dress still felt sweetly Reese.

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PASTEL PRINCESS, 2004

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At the Venice Film Festival, Reese experimented with a ladylike shade, choosing a pleated Carolina Herrera cocktail dress in soft blue.

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BLACK & WHITE BEAUTY, 2005

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The screen star’s girlie style came through at the L.A. premiere of Just Like Heaven, where she stunned in a beaded, tulle Monique Lhuillier number with a flattering black waistband.

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SMILES & SPARKLES, 2006

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At the 2006 Oscars, Reese snagged a statue for her performance in Walk the Line and earned a spot on many best-dressed lists with her stunning jewel-accented vintage Christian Dior gown.

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SUNSHINE SWEETHEART, 2007

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Reese proved yellow can very sexy in a Nina Ricci strapless sheath paired with red Brian Atwood sandals and sparkly bangles at the Golden Globes.

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SCENE STEALER, 2009

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She may have been there to present the award for Best Director, but Reese s stunning black-and-blue Rodarte gown with an ombre skirt and asymmetrical beading at the bodice got all the (much deserved!) attention at the 2009 Oscars.

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METALLIC MAMA, 2009

Credit: Jon Kopaloff/Filmmagic

No mom jeans for this family woman! Reese posed on the red (er, blue) carpet in another Rodarte dress for the Monsters vs. Aliens premiere in L.A., showing off her banging body in a futuristic silver-and-green mini.

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PRETTY IN PEPLUM, 2010

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The black-and-blue combo shows up yet again, but this time it’s a flirty Jason Wu frock with a belted waist at the Vital Voices 2010 Global Leadership Awards.

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BLONDE BOMBSHELL, 2010

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At the Avon Foundation for Women Gala, Reese brought major sex appeal with another ruffled Jason Wu strapless dress, paired with peep-toe pumps and wavy hair.

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OLD HOLLYWOOD, 2011

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Considered one of the most classic Oscars gowns of all time, the actress walked the carpet in a black, curve-hugging Armani Privé gown with white trim, topped off with a high ponytail.

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TRÈS BELLE, 2011

Credit: Tony Barson/Filmmagic

At the Paris premiere of Water for Elephants, the star was seeing red in a beautifully draped, asymmetrical Giambattista Valli dress that showed off her toned gams and arms.

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WILD CHILD, 2011

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Rocking a Zac Posen leopard-print mini, nude pumps and beachy waves, Reese attended the MTV Movie Awards where she received the generation award (looking a full generation younger than she is!).

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COBALT QUEEN, 2011

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Continuing to show plenty of skin, Reese selected an ultra-sexy off-the-shoulder custom Stella McCartney bustier dress and nude peep-toe heels for the London premiere of Water for Elephants.

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ALL BUSINESS, 2011

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One of the hardest working women in the biz selected a 9-to-5-inspired suit by Bocanegra, but kept up her sexy streak by pairing it with a lacy shell to the Annual Women in Hollywood Tribute.

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PLAYING PEEKABOO, 2011

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For the LACMA Inaugural Art and Film Gala last year, Reese injected a bit of edginess into her look with a body-conscious Cushnie et Ochs LBD.

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RED HOT, 2012

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Reese s crimson Zac Posen gown (worn at the Golden Globes) easily earned her a spot on our best dressed of the season list – it flattered her petite, curvy figure perfectly.

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SHINE ON, 2012

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Color us green with wardrobe envy! For the London premiere of This Means War, the leading lady was flirty and feminine in a gleamy black-and-green mini featuring tiered detailing at the hem.

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OFF-DUTY CHIC, 2012

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After a career s worth of sartorial success on the red carpet, Reese has honed an equally stylish street style. Case in point: This printed Kate Spade New York dress paired with a structured satchel and classic flats for a day out in Santa Monica, Calif.

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MELLOW YELLOW, 2012

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To promote This Means War in Rio de Janeiro, Reese donned a cheery Louis Vuitton dress with a waist-cinching black belt. A sparkly statement necklace and black ankle-strap sandals completed the look.

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By Catherine Dash