Movie Awards: MTV Generation Award Winner Reese Witherspoon's Iconic Fashion Moments

Guys. The 2011 MTV Movie Awards are upon us, and of course, we'll have our eyeballs glued to the red carpet for all the most memorable moments but the announcement that holds us in THRALL right now is the fact that the coveted MTV Generation Award is being presented to none other than the elegant and talented Reese Witherspoon. The woman's range is unbelievable, from winning an Oscar for a poignant American biopic AND starring in an awesomely campy blockbuster that yielded multiple sequels (not to mention a Broadway musical). This award is totally 250 percent deserved, so in honor of this esteemed accomplishment and Reese's epic career, we're taking a look back at her top 10 most iconic movie looks. Again, for us, it's all about the FASHION.


Reese Witherspoon as Marlena Rosenbluth in 'Water for Elephants.'
Photo: Courtesy of Twentieth Century Fox

Character: Marlena Rosenbluth

Costume Design by: Jaqueline West

The Look: With platinum finger waves, tight curls, and elegant, figure-flattering cuts, Reese channels Jean Harlow in the old Hollywood glamour of Water for Elephants. Even in casual wear, she's dressed to the nines in a nautical striped belted top, a white midi-length pencil skirt, and a smart white beret. Very Gaultier of a certain period.


Reese Witherspoon as Melanie Smooter in 'Sweet Home Alabama'.
Photo: Courtesy of Touchstone Pictures

Character: Melanie Smooter

Costume Design by: Sophie Carbonell

The Look: From this Sophie Carbonell-helmed wardrobe, we get the dynamic interplay of City vs. Country. To really drive home that Witherspoon's character is from New York and works in fashion, she cuts Reese's mane into a choppy 'do and puts her in all black to contrast with the denim and T-shirts of her hometown. While the funereal hue might not be all that practical in the heat, this movie also did feature a proposal at Tiffany's, which is NOT entirely appropriate for a designer and politician. Can you imagine the paparazzi?

8. FEAR (1996)

Reese Witherspoon as Nicole Walker in 'Fear.'
Photo: Courtesy of Universal Pictures

Character: Nicole Walker

Costume Design by: Kirsten Everberg

The Look: In this film, Reese is full-on vintage '90s. The crew-neck baby tee plus an A-line mini with buttons on the front is VERY quintessential '90s casual wear. Not that you need even more '90s cues when your boyfriend is (a disturbingly hot) Marky Mark. AMIRITE?

7. ELECTION (1999)

Reese Witherspoon as Tracy Flick in 'Election.'
Photo: Courtesy of Paramount Pictures

Character: Tracy Flick

Costume Design by: Wendy Chuck

The Look: As the consummate overachiever Tracy Flick, Reese's style was relatively uniform and preppypreppypreppy. Throughout the film, she rocked an impressive array of sweater vests, crisp button-ups, and hair that was always pulled in a pony or worn in shrewy, short curls. The uptight, neck-vein intensity was styled PERFECTLY.


Reese Witherspoon as Jennifer in 'Pleasantville.'
Photo: Courtesy of New Line Cinema

Character: Jennifer

Costume Design by: Judianna Makovsky

The Look: Though Pleasantville starts out in the '90s, most of the film is set in the fictional town of the same name in the '50s. The wardrobe is all era-appropriate resplendent with pincurls, shrunken sweaters, and exaggerated waistlines with full skirts. Dior New Look gone high school and lovely.


Reese Witherspoon as Evelyn Williams in 'American Psycho.'
Photo: Courtesy of Lions Gate Films

Character: Evelyn Williams

Costume Design by: Isis Mussenden

The Look: Reese's look in American Psycho is like a time capsule of that weird transitory period where the late '90s still looks HELLA '80s. More-is-more louche cuts and brash colors that speak to richesse and FUR APLENTY. This is where we pour some out for that razor straight one-length 'do, ancestor of the blunt-cut bang. Hard to pull off but a *golf clap* for those who do.

4. WALK THE LINE (2005)

Reese Witherspoon as June Carter in 'Walk the Line.'
Photo: Courtesy of Twentieth Century Fox

Character: June Carter

Costume Design by: Arianne Phillips

The Look: Reese's look in the biopic Walk the Line needed to be emblematic of June Carter, which meant ladylike dress shapes, long loose curls, a HELLUVA lot of hair spray, dresses that'd make any vintage collector drool, and a steely disposition with an iron backbone. Note: She never ONCE suffered from looking costumey due to her unflappable acting chops.

3. FREEWAY (1996)

Reese Witherspoon as Vanessa Lutz in 'Freeway.'
Photo: Courtesy of The Kushner-Locke Company

Character: Vanessa Lutz

Costume Design by: Merrie Lawson

The Look: Freeway is set and filmed in a time when horizontal stripes (sometimes in Neapolitan ice-cream colors IN TERRY CLOTH) and the crop-top were king. The entire wardrobe for this movie could have been bought at one of those smaller mall stores that has a vaguely feminine-sounding name like "Pineapple" or has too many odd numbers—"5, 7, 9"—but make no mistake, these then-ubiquitous togs would make a KILLING at ironic vintage stores and eBay stores now.


Reese Witherspoon as Annette Hargrove in 'Cruel Intentions.'
Photo: Courtesy of Columbia Pictures

Character: Annette Hargrove

Costume Design by: Denise Hargrove

The Look: As the virgin Annette Hargrove, Reese was styled in a lot of pastels. Her hair was cut into a modified "Rachel" (very de rigeur at the time) and when it wasn't falling in sweet layers, it was braided into pigtails or something equally innocent. The demure allure was best evidenced by crisp white button-ups or dainty jewelry. Also, books.


Reese Witherspoon as Elle Woods in 'Legally Blonde.'
Photo: Courtesy of Metro-Goldwyn-Mayer

Character: Elle Woods

Costume Design by: Sophie Carbonell

The Look: The wardrobe for Legally Blonde is deliciously kitschy. And how could it not for an over-the-top character like Elle Woods? This styling is all about candy colors straight out of the Barbie Dream House and crazy fabrics used in ways that would be shockingly ravishing IRL, like this magenta jacket-skirt-combo.

Watch the 2011 MTV Movie Awards on Sunday, June 5, at 9 p.m. ET/PT on MTV.


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