Then and Now: The Evolution of Reese Witherspoon

Then and Now: The Evolution of Reese Witherspoon
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Photo: Getty

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.

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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.

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October 1991
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.

Photo: Getty
February 1993
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.

Photo: Getty
July 1995
July 1995

At the premiere of Waterworld, of course.

Photo: Getty
May 1997
May 1997

Having a serious Nineties moment.

Photo: Getty
February 1999
February 1999

OK, it was a bit of a strange style choice. But—this was at the Cruel Intentions premiere!

Photo: Getty
July 2001
July 2001

Fresh-faced at the Legally Blonde premiere.

Photo: Getty
June 2003
June 2003

Witherspoon arrived pregnant with son Deacon Reese Phillippe for the Legally Blonde 2 premiere.

Photo: Getty
September 2004
September 2004

Back on the red carpet after giving birth to Deacon, Witherspoon gave brown hair a spin at the Venice Film Festival.

Photo: Getty
November 2005
November 2005

With her husband at the time, Ryan Phillippe, at the premiere of Walk The Line in New York.

Photo: Getty
March 2006
March 2006

Witherspoon won the Best Actress in a Leading Role award for Walk the Line at the Academy Awards this year.

Photo: Getty
January 2007
January 2007

In full Reese Witherspoon mode at the Golden Globes.

Photo: Getty
January 2009
January 2009

Remember when she dated Jake Gyllenhaal?! Yeah, we'd forgotten that one too.

Photo: Getty
December 2010
December 2010

With son Deacon and daughter Ava, receiving her Hollywood Walk Of Fame Star.

Photo: Getty
April 2011
April 2011

With Taylor Swift at the Academy Of Country Music Awards—highlighting how tiny Witherspoon really is!

Photo: Getty
December 2012
December 2012

With Jim Toth, her new husband.

Photo: Getty
February 2013
February 2013

At the Oscars, looking regal AF.

Photo: Getty
March 2014
March 2014

At the Vanity Fair Oscar Party, looking sleek and lovely.

Photo: Getty
May 2015
May 2015

At the Met Gala. Does Witherspoon ever not look put together on a red carpet? We vote no.

Photo: Getty
February 2016
February 2016

Back at the Academy Awards!

Photo: Getty
February 2016
February 2016

Grabbing coffee in L.A., proving that she can also do casual-cool.

Photo: Getty
February 2017
February 2017

With her complete lookalike daughter Ava at the Big Little Lies premiere.

Photo: Getty

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  • October 1991
  • February 1993
  • July 1995
  • May 1997
  • February 1999
  • July 2001
  • June 2003
  • September 2004
  • November 2005
  • March 2006
  • January 2007
  • January 2009
  • December 2010
  • April 2011
  • December 2012
  • February 2013
  • March 2014
  • May 2015
  • February 2016
  • February 2016
  • February 2017
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