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Then and Now: The Evolution of Reese Witherspoon

Bibi Deitz is the News Editor at STYLECASTER. She holds an MFA in fiction writing from Bennington College and lives in Brooklyn. Recent work has appeared in The Wall Street Journal, Bustle, Marie Claire, Teen Vogue, The Huffington Post, ...

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The evolution of Reese Witherspoon

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The evolution of Reese Witherspoon

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.

More: The 60 Most Naked Celebrity Instagram Photos of All Time

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 blond 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.

More: The 30 Most (NOT-FAMOUS!) Naked Women on Instagram

 

Originally posted on StyleCaster.

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February 1993

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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

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July 1995

At the premiere of Waterworld, of course.

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May 1997

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May 1997

Having a serious '90s moment.

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February 1999

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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

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July 2001

Fresh-faced at the Legally Blonde premiere.

 

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June 2003

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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

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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

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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

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March 2006

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

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January 2007

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January 2007

In full Reese Witherspoon mode at the Golden Globes.

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January 2009

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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

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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

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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

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December 2012

With Jim Toth, her new husband.

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February 2013

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February 2013

At the Oscars looking regal AF.

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March 2014

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March 2014

At the Vanity Fair Oscar Party looking sleek and lovely.

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May 2015

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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

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February 2016

Back at the Academy Awards!

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February 2016 2

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February 2016 2

Grabbing coffee in LA proving that she can also do casual-cool.

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February 2017

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February 2017

With her complete look-alike daughter Ava at the Big Little Lies premiere.

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