:max_bytes(150000):strip_icc()/GettyImages-2171591930-8630e1c3ae6a4355b42efe4989ef1de8.jpg "Reese Witherspoon’s Best Red Carpet Looks")
Reese Witherspoon has been in the spotlight since the ’90s, and her style has undergone quite the transformation since then. First there was the dominance of Y2K-era style—think space buns, maxi skirts, and low-rise jeans—followed by the somewhat questionable trends of the early aughts. Then there was the 2010s, and with it came side bangs, skinny jeans, and the graphic tee. Perhaps it goes without saying: looking at this laundry list of trends, sartorially speaking, we’ve come a long way since then. And for Witherspoon in particular, her look has evolved into one that embodies casual elegance, strapless gowns, and lots of twinning moments with her daughter, Ava Phillippe.
From skyrocketing to fame in 1999 thanks to Cruel Intentions to winning her first Oscar for Walk The Line in 2006 and taking home Emmy after Emmy for Big Little Lies, Witherspoon has been hard at work for decades—stylistically and otherwise. Ahead, step back in time to watch her style evolution unfold, from 1994 to 2024.
Ivory Appliqué
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After a few years of absence from the Emmys red carpet, Witherspoon returned with two nominations for her acting and producing of The Morning Show. She wore a strapless Dior gown for the occasion, covered in delicate floral appliqués and paired with a diamond choker necklace.
Lady in Red
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Witherspoon stuck to her love of strapless gowns for an appearance at the 30th Annual SAG Awards, where she was nominated, once again, for her role in The Morning Show.
“It’s giving Pookie looks fire,” she joked with Laverne Cox, in reference to the TikTok star Campbell Hunt Puckett. “It’s giving lady in red.”
Seeing Double
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Witherspoon was joined by her lookalike daughter at the 2024 Critics Choice Awards, where both women went strapless—a Monique Lhuiller minidress for Ava Phillippe, and a Celine gown for Witherspoon.
Nostalgic Pink
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Witherspoon joined her The Morning Show co-star (and co-anchor) Jennifer Aniston at the 2024 Golden Globes wearing a black Monique Lhuillier gown with just a touch of Legally Blonde-inspired pink up top.
Red Hot
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Witherspoon teamed up with Dior once again for the 2021 Oscars, where she wore a fire engine red gown cinched at the waist with a black belt.
Power Suit
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Witherspoon celebrated the premiere of Truth Be Told in 2019 with a black power suit and a pussy bow blouse, the combination of which was a notable departure from her typical red carpet attire.
Blazer Dress
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The actress arrived at the 2017 Emmys in a satin blazer dress from Stella McCartney, complete with Christian Louboutin heels and diamond jewelry. It was an outfit fit for a celebration: that night, Witherspoon took home an Emmy for her role as executive producer on Big Little Lies.
Couture Gown
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Witherspoon returned once again to her safe space—the strapless gown—with a stunning Oscar de la Renta couture number for the 2016 Oscars. She balanced out the stiff formality of the gown with loose, undone hair and minimal jewelry.
Timeless Tom Ford
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Witherspoon tapped Tom Ford for the 2015 Oscars, opting for a chic black and white off-the-shoulder gown, paired with diamonds courtesy of Tiffany & Co.
A Case for Color
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Fresh off her stint playing Cheryl Strayed in Wild, Witherspoon arrived at the 2014 Golden Globes in a long teal gown and a very 2010s beauty look: side bangs.
Archival Dior
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Witherspoon selected a stunning 1955 gown from the Dior archive for the 2006 Academy Awards, where she took home the Oscar for best actress for her role in Walk The Line.
Oscars Debut
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For her 2002 Academy Awards debut, Witherspoon donned a lacy black dress from Valentino. With her short barrel-curled bob and a vintage handbag, the ensemble was very 1920’s flapper girl-coded.
Maxi Skirt
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Very few films can claim to have rocked the Y2K zeitgeist in the way that Cruel Intentions did. For the film’s premiere—which happened just a few months before Witherspoon and her fellow co-star, Ryan Phillippe, tied the knot—the actress wore a pink maxi skirt and a long white blouse.
Space Buns
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Witherspoon rocked space buns, a spaghetti strap tank-top, and a black maxi skirt at the 1997 premiere of Nowhere, a sci-fi comedy starring James Duval and Christina Applegate.
’90s Minimalism
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In the era before professional stylists ruled the red carpet, Witherspoon put together her own ensemble that very much embodied the style of 1994: a black maxi dress, a cross-body bag, and a fresh-faced beauty look.
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