Reese Witherspoon's Best Looks of All Time

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.

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.

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

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.

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.

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.

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.

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.

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.

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.

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.

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.

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!).

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.

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.

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.

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.

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.

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.

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.