Fame10 Fashion Evolution: Reese Witherspoon

Reese Witherspoon’s fashion has really evolved since she first began acting. We’ve watched her through the years and the transformation has been quite impressive. She’s had many awkward moments, but she’s always followed them up with many, many stylish ones as well. There were a few years there when she was with Ryan Phillippe where she seemed to be trapped in her “Legally Blonde” sort of style; however, since splitting from him, she’s become a bonafide fashionista. Because Reese is so talented and so fashionable, join us as we take a look at her amazing fashion evolution!

Teen Choice Awards – 2001

Reese Witherspoon dressed an awful lot like her character from “Legally Blonde” at the 2001 Teen Choice Awards. Like Elle Woods, she is donning an excessive amount of pink. Considering she was married with a child at this point, one would think that she would have dressed less like a girl and more like the sophisticated young woman that she was.

Witherspoon’s career had really started to take off at this point. The film “Legally Blonde” was a box office hit and it also earned her rave reviews, as well as a Golden Globe nomination. Before this, she was more of a supporting player in films; however, “Legally Blonde” firmly established her as one of Hollywood’s leading ladies. When the sequel came out, Witherspoon commanded a $15 million paycheck. Sadly “Legally Blonde 2: Red White and Blonde” wasn’t the hit that its predecessor was. Critics were generally unimpressed with the script, but they still liked Witherspoon.

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Teen Choice Awards – 2002

The “Legally Blonde” star dressed casually for the 2002 Teen Choice Awards. She wore these beige linen dress pants with a black and pink tank top and pink heels. We really love the pants. They look so comfortable but fashionable at the same time. We are getting tired of all the pink though. We much prefer what Selma Blair is wearing. That jewel-encrusted skirt is super cute and so are the layered tank tops. Blair is proof that a girl can look good at an event without wearing any pink.

Professionally, 2002 wasn’t a bad year for the blonde actress. She starred in the film adaptation of Oscar Wilde’s play “The Importance of Being Earnest,” as well as a romantic comedy, “Sweet Home Alabama,” alongside Josh Lucas and Patrick Dempsey. The latter became her biggest box office hit to date. Unfortunately the critics weren’t overly impressed with the film. They gave it mostly negative reviews.

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Premiere of Vanity Fair – 2004

Reese Witherspoon looked gorgeous at the premiere of “Vanity Fair” in this sleek orange dress. It shows just enough cleavage to be classy and sexy. Who knew that she looked so good with brown hair! We love how it warms her skin tone and really brings out her blue eyes. She should forget blonde hair and keep her hair brown. It suits her so well.

When Witherspoon was filming “Vanity Fair,” she was five months pregnant with her son, Deacon; however, this didn’t end up becoming a problem. Director Mira Nair was quite accommodating, making sure to hide the actress’ growing bump with voluminous period dresses and by strategically placing her behind pieces of furniture. Witherspoon believes that being pregnant helped her with her portrayal of her character. “I love the luminosity that pregnancy brings, I love the fleshiness, I love the ample bosom – it gave me much more to play with,” she said.

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Premiere of Just Like Heaven – 2005

The “Sweet Home Alabama” star wore this jewel-encrusted Monique Lhuillier dress with a ‘60s-inspired hairstyle to the premiere of the romantic comedy/fantasy film “Just Like Heaven.” While we think the dress is quite pretty, we can’t help but feel that it looks a bit too much like a prom dress. We would have preferred something sleeker like the dress she wore the premiere of “Vanity Fair.”

The film “Just Like Heaven” did pretty well at the box office; however, critics were pretty ambivalent about it. Rotten Tomatoes’ consensus on the movie was “Delightfully sweet like a lollipop, Just Like Heaven is a dreamy romantic comedy that may give you a toothache when it attempts to broach difficult end of life issues by throwing a cherry on top.” Reese Witherspoon’s performance was well received, but she’s going to need a lot more than a romantic comedy for her to get the Academy’s attention.

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78th Annual Academy Awards – 2006

Reese Witherspoon looked stunning at the 78th Annual Academy Awards. She donned this vintage Christian Dior gown, which featured a V-neck and metallic embellishments. She reportedly found the dress while shopping at a vintage shop in Paris and had it fixed up so that she could wear it to the Oscars.

That night, Witherspoon took home the Academy Award for Best Actress for her portrayal of June Carter Cash in “Walk the Line.” The film was a huge success on a critical and commercial level. Her performance received rave reviews from the critics. Baltimore Sun reviewer Michael Sragow was one critic who was especiall impressed with her and Joaquin Phoenix. “What Phoenix and Witherspoon accomplish in this movie is transcendent. They act with every bone and inch of flesh and facial plane, and each tone and waver of their voice. They do their own singing with a startling mastery of country music’s narrative musicianship,” he wrote.

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79th Annual Academy Awards – 2007

Never one to disappoint, the Oscar-winning actress showed up at the 79th Annual Academy Awards in this purple tiered Nina Ricci gown by Olivier Theyskens with jewels from Van Cleef & Arpels. She actually worked on the design of the dress with Theyskens. She chose the color and gave specific instructions to the designer on the length: She was adamant that it be a show-stopping, to-the-floor gown.

This particular year, Witherspoon arrived at the Academy Awards without a date. She and husband Ryan Phillippe had broken up several months before, not long after she took home her Best Actress Oscar. Many believe that the marriage ended because he was having an affair with Abbie Cornish, his co-star from “Stop-Loss.” Both Phillippe and Cornish denied having an affair; however, as soon as he separated from Witherspoon, these two took their relationship public. Naturally this didn’t do anything good for the actor’s reputation.

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Premiere of Four Christmases – 2008

Reese Witherspoon channeled old Hollywood glam for the premiere of “Four Christmases.” She rocked this navy satin Nina Ricci bustier dress, which featured beaded embroidery and a bustled hem, with gold jewelry. She reportedly teamed up again with Oliver Theyskens to design this dress. We really like it; however, we much prefer the other gown that they collaborated on for the 2007 Academy Awards.

After winning an Oscar two years before, Witherspoon seemed to be struggling professionally. Many of her films received mixed or negative reviews. “Four Christmases,” which co-starred Vince Vaughn, did not fare well with the critics. The Hollywood Reporter called it “one of the most joyless Christmas movies ever” with “an unearned feel-good ending [that] adds insult to injury.” The Associated Press was equally unimpressed, asserting that the film “began with some promise” then segued into “noisy joylessness [that] sets the tone for the whole movie.” The only good thing about this film is that it did reasonably well at the box office.

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Premiere of Monsters vs. Aliens – 2009

At the premiere of “Monsters vs. Aliens,” this Golden Globe-winning actress looked sexy in this this short, space-aged Rodarte Fall 2009 silver and green dress. She completed the look with grey Balenciaga peep-toe heels. This is definitely one of the edgier outfits that we’ve seen her in. She seems to know this too, which is why she is standing there with her hand on her hip, glaring at the camera. We haven’t seen this kind of attitude from her up until this point!

“Monsters vs. Aliens” was one of Reese Witherspoon’s only successful post-Oscar films, but we think it fails to really utilize her talents. Critics weren’t overly impressed with this computer-animated 3-D feature film; however, many did give it favorable reviews. The only real complaints that some reviewers had were that it lacked wit or depth. In spite of this, it still did really well at the box office.

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Hollywood Walk of Fame Star Ceremony – 2010

Reese Witherspoon showed up to receive a star on the Hollywood Walk of Fame looking like a million bucks. Joined by her two children Ava and Deacon and one of her puppies, she accepted the honor in style. She wore a red and black polka dot Dolce & Gabbana dress, bright red Jimmy Choo heels and Bochic jewelry. All in all, this is one of her best looks yet.

2010 wasn’t the most exciting year professionally for Witherspoon. She had taken a bit of a break and had just returned to the big screen with “How Do You Know,” which co-starred Paul Rudd, Owen Wilson and Jack Nicholson. Unfortunately, the film was a box office failure, only grossing 40% of its $120 million budget, as well as a critical disaster. LA Times has listed the film as one of the most expensive box office flops of all time. Poor Witherspoon seemed to have fallen victim to the Oscar curse!

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MTV Movie Awards – 2011

The “Walk the Line” star looked smoking hot at the 2011 MTV Movie Awards in this Zac Posen Leopard Print Jacquard Bustier Dress from the designer’s Pre-fall 2011 collection, which she paired with nude heels, earrings and a gold cuff by Neil Lane. That evening, she was given the Generation Award.

Reese Witherspoon gave quite the speech that night, slamming celebrities like Paris Hilton and Kim Kardashian. “I get it, girls, that it’s cool to be a bad girl. But it is possible to make it in Hollywood without doing a reality show,” she said. “When I came up in this business, if you made a sex tape, you were embarrassed and you hid it under your bed. And if you took naked pictures of yourself on your cell phone, you hide your face, people!” It sounds like reasonable advice; however, how many young celebrities are actually going to take it?

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Premiere of Mud – 2012

Reese Witherspoon stunned at the premiere of “Mud.” She wore this custom-made navy silk chiffon Atelier Versace gown, which was covered in Swarovski crystals and featured a cutout back. She accessorized with silver Versace shoes and Chopard jewels. Shortly after splitting from Jake Gyllenhaal in 2010, Witherspoon quickly moved on to Jim Toth, a Hollywood agent. These two wasted no time. They were married a year later and soon after that they were expecting their first child together.

While all was well in her personal life, the pregnant actress was still struggling to get her career back on track. None of the romcoms she was starring in were doing anything for her career. They only offered a good paycheck – nothing else. The film “Mud” was definitely a step in the right direction. It received universal acclaim from critics, marking a dramatic change in Matthew McConaughey’s career. If he can escape the romcom curse, we have total faith that Witherspoon can too.

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85th Academy Awards – 2013

The talented actress looked regal at the 85th Academy Awards in this cobalt blue Louis Vuitton gown with black accents. According to her, her daughter Ava helped her pick it out! “I love the color of it. My daughter and I picked it out. She said, this is a winner. She’s 13, so she definitely weighs in. She helps me pick the jewelry, makeup and everything,” she said.

Months after the Academy Awards, Reese Witherspoon found herself in hot water after she cussed out a police officer who was arresting her husband for DUI. Because of her belligerence, the officer arrested her for disorderly conduct. For the first time in her career, Witherspoon had to suddenly give the public an explanation for her behavior. “I clearly had one drink too many and I am deeply embarrassed about the things I said,” she said in a statement. We sure hope that she learned her lesson!

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Lupus LA Bag Ladies Luncheon – 2014

Reese Witherspoon switched things up for the Lupus LA Bag Ladies Luncheon. She wore this Self-Portrait dress, which featured a blue metallic floral pattern with an opaque lining. She completed the look with white Christian Louboutin pumps and an Edie Parker clutch. Not just anyone could pull off a dress like this, but we think she makes it work. Also, we love seeing her in blue. It is definitely one of her best colors.

Almost a decade after winning an Academy Award for her role in “Walk the Line,” Witherspoon seems to finally have her career back on track. She’s done with the silly romcoms and she’s back in the game with a couple of Oscar-baity dramas, “The Good Lie” and “Wild.” People have been talking about Witherspoon a lot and it sounds like she’s probably going to be an awards contender this time around. Don’t be too surprised if she takes home another Academy Award in 2015!

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Cate has a B.A. and an M.A. in English Literature and has been the Managing Editor of Fame10 for more than 6 years. Despite having a love for the works of Thomas Hardy, Leo Tolstoy and Lord Byron, she also has an intense fascination with pop culture. When she isn’t writing for Fame10, she’s planning her next big adventure in Southeast Asia.