Reese Witherspoon Can Pull Off Any Hairstyle, But Her Retro Looks Are Always Special

She’s a chameleon.

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Reese Witherspoon’s sunny disposition has been a movie screen mainstay since the early ’90s, but the star has only gotten more stylish with time. In a look back at the actor’s beauty evolution, watch her grow from trendy teenager to the sophisticated A-lister she is today.

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It doesn’t get much more 1997 than a 21-year-old Witherspoon done up in tiny top knots and pale blue eyeshadow — a perfect match for her blue camisole and trio of chokers, naturally.Ron Galella, Ltd./Ron Galella Collection/Getty Images
As a young Witherspoon padded her resume with several films set in high school through the late ’90s, she channeled her burgeoning maturity on the red carpet. Often experimenting with smoky eyeshadow and red lipstick, her medium-length naturally blond hair was a constant.Ron Galella, Ltd./Ron Galella Collection/Getty Images
At 2001’s Legally Blonde premiere, film star Witherspoon played homage to Elle Woods’ signature look with pretty pink eyeshadow, blush, and lipstick in similar tones of violet. Her love for colorful makeup was a through-point in her 20s.Frank Trapper/Corbis Entertainment/Getty Images
Just three years later, Witherspoon’s new brunette hair shocked fans. While the deep brown color was for a role (which would all prove to be very worth it the next year), the actor decided to keep it for a while in real life, too.J. Vespa/WireImage/Getty Images
The actor’s portrayal of June Carter Cash required nearly a year of brunette hair, but she seemed pretty happy with the tradeoff when she won the Best Actress Oscar in 2005 — with her buttery blond restored in time for the red carpet.Ian West - PA Images/PA Images/Getty Images
Do you remember where you were when Witherspoon arrived at the Golden Globes with this incredible set of side-bangs? One of her first high-profile events after news of her divorce from Ryan Phillippe broke, it’s a textbook example of a killer “revenge haircut.”Frazer Harrison/Getty Images Entertainment/Getty Images
After saying goodbye to the bangs, Witherspoon got reacquainted with her love for edgy makeup. This smoldering 2010 look features multiple shades of smudgy, sultry eyeshadow, all framed by her new middle part.Jon Kopaloff/FilmMagic/Getty Images
Who can deny Witherspoon’s Old Hollywood charm? The star doesn’t opt for vintage-inspired looks terribly often, but these retro, side-swept curls and winged eyeliner are next-level lovely.Steve Granitz/WireImage/Getty Images
The actor’s signature shade of pale, warm-toned blond hit new lengths by 2017, the same year she won an Emmy for Big Little Lies’ outstanding first season — her very 2010s center part still going strong.Dan MacMedan/Getty Images Entertainment/Getty Images
After growing her hair out longer than it’d ever been, Witherspoon shook things up in 2020 with a major chop. Her shoulder-clearing bob featured so much body and movement, especially when curled. At the 2020 Oscars, she’s again aesthetically inspired by the stars of yesteryear.Toni Anne Barson/WireImage/Getty Images
2023 saw the return of several classic Witherspoon beauty hallmarks, like longer hair, a deep side part, and bolder makeup. At the premiere of her Netflix movie Your Place Or Mine with Ashton Kutcher, her eyes are rimmed with a shimmery bronze shade that emphasizes her eye color, along with bright pink blush.Steve Granitz/FilmMagic/Getty Images

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