Then and Now: The Evolution of Reese Witherspoon
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If you’ve been watching Big Little Lies (or catching Legally Blonde—no shame), you’ve been seeing a lot of Reese Witherspoon of late. But do you remember what she looked like back in the day? Witherspoon rose to fame in the ’90s, before some starlets were even born (paging Bella Hadid and Kendall Jenner) and long before Witherspoon’s doppelgänger daughter, Ava Phillippe, was even a sparkle in her mother’s eye.
So—we traced Witherspoon’s most iconic looks, from all the way back in 1991 until the present day, to have a closer look at the star’s transformation over the years that span her career. We scanned hundreds of images taken over the course of over a quarter of a decade to find the best of the best, so you can really get a good idea of where Witherspoon came from—and where she’s headed next. She’s always had that trademark blonde hair (except for a quick foray into darker territory!) and she seriously hasn’t aged since the ’90s. Ahead, the evolution of Witherspoon from all the way back in the day until now.
October 1991
There's a lot going on in this pic—one of the oldest industry pics of Witherspoon out there. What's going on with her hair? We have no idea, but one thing is for sure: We'd wear that shirt in a heartbeat.
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February 1993
Remember when Chris O'Donnell and Witherspoon dated? Yeah, we didn't either. But here they are together, with Witherspoon in quite the red dress.
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July 1995
At the premiere of Waterworld, of course.
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May 1997
Having a serious Nineties moment.
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February 1999
OK, it was a bit of a strange style choice. But—this was at the Cruel Intentions premiere!
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July 2001
Fresh-faced at the Legally Blonde premiere.
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June 2003
Witherspoon arrived pregnant with son Deacon Reese Phillippe for the Legally Blonde 2 premiere.
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September 2004
Back on the red carpet after giving birth to Deacon, Witherspoon gave brown hair a spin at the Venice Film Festival.
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November 2005
With her husband at the time, Ryan Phillippe, at the premiere of Walk The Line in New York.
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March 2006
Witherspoon won the Best Actress in a Leading Role award for Walk the Line at the Academy Awards this year.
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January 2007
In full Reese Witherspoon mode at the Golden Globes.
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January 2009
Remember when she dated Jake Gyllenhaal?! Yeah, we'd forgotten that one too.
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December 2010
With son Deacon and daughter Ava, receiving her Hollywood Walk Of Fame Star.
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April 2011
With Taylor Swift at the Academy Of Country Music Awards—highlighting how tiny Witherspoon really is!
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December 2012
With Jim Toth, her new husband.
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February 2013
At the Oscars, looking regal AF.
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March 2014
At the Vanity Fair Oscar Party, looking sleek and lovely.
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May 2015
At the Met Gala. Does Witherspoon ever not look put together on a red carpet? We vote no.
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February 2016
Back at the Academy Awards!
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February 2016
Grabbing coffee in L.A., proving that she can also do casual-cool.
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February 2017
With her complete lookalike daughter Ava at the Big Little Lies premiere.
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