42 photos that show how Reese Witherspoon's style has evolved over the years

Publish date: 2024-08-30

Witherspoon often gravitates toward pieces that seem to be influenced by whatever project she's working on; for example, she wore pink pieces while promoting the " Legally Blonde " franchise, and an ethereal gown to the premiere of"Just Like Heaven."

Work-inspired ensembles aside, the actor has a distinct personal fashion aesthetic that lives at the intersection of vintage and modern . From cardigans and combat boots to glamorous gowns and heels, keep scrolling to see how Witherspoon's style has changed since 1996.

In July 1999, Reese Witherspoon wore a grunge-meets-glam ensemble to "The Fear" premiere in Sydney, Australia.

Patrick Riviere/Getty Images

For a perfectly '90s look, the actor paired a maroon maxi dress with a cropped, sequin-emblazoned cardigan and combat boots.

At the Los Angeles, California, premiere of "Cruel Intentions" in February 1999, she paired a baby doll top with a maxi skirt.

Brenda Chase / Stringer

Witherspoon quite literally tied her outfit together with a thingold belt.

In May 2000, she wore a strapless gray dress to the Sixth Annual Blockbuster Entertainment Awards in Los Angeles, California.

Patrick Riviere/Getty Images

Witherspoon completed her monochromatic ensemble by pinning her hair back and layering on eyeliner.

She fittingly wore an all-pink ensemble to the July 2001 premiere of "Legally Blonde" in Los Angeles, California.

Vince Bucci/Getty Images

The actor added dimension to the outfit by layering a black mesh slip over her pink dress.

Once again, Witherspoon mixed grunge and preppy pieces at the August 2002 The Teen Choice Awards in Los Angeles, California.

Kevin Winter/Getty Images

The actor paired a Ralph Lauren logo top with a pair of flaredcorduroypants.

Witherspoon wore a mixed-material dress to the New York City premiere of "Sweet Home Alabama" in September 2002.

Matthew Peyton/Getty Images

Witherspoon completed her shimmery, color-coordinated look with a smoky eye.

In June 2003, she wore a floral dress to the premiere of "Legally Blonde 2: Red, White & Blonde" in Southampton, New York.

Matthew Peyton/Getty Images

She topped off her summery ensemble with strappy heels and bright, shimmery makeup.

In August 2004, Witherspoons outfit for a New York City screening of "Vanity Fair" really popped thanks to her dark brown hair.

Evan Agostini/Getty Images

She finished her outfit with matching golden accessories like a purse, a pair of shoes, and earrings.

In September 2005, the actress looked more like herself at the premiere of "Just Like Heaven" in Los Angeles, California.

Kevin Winter/Getty Images

Witherspoon wore an ethereal white tulle dress with an illusion neckline.

Witherspoon wore a mermaid-style red dress to the November 2005 premiere of "Walk The Line" in New York City.

Paul Hawthorne/Getty Images

The dress had a vintage-glam feel with an oversized bow cinching the top.

She went for another metallic look at the 2006 Golden Globes, which were held in Beverly Hills, California.

Frazer Harrison/Getty Images

Witherspoon added a touch of color with her rosy pink lipstick.

The actor wore an embellished, champagne-colored gown to the Oscars in 2006.

Frazer Harrison/Getty Images

She completed her ensemble with dark eye makeup and warm, shimmery lipstick.

The actor changed things up for the January 2007 Golden Globes when she wore a bright yellow minidress with red heels.

Frazer Harrison/Getty Images

She topped off her look with one chunky bracelet, red lipstick, and dark eye makeup.

The next month, she wore a tiered, purple gown to the Oscars in Hollywood, California.

Vince Bucci/Getty Images

The actor kept her hair and makeup simple for the red carpet event.

She went for a decidedly glamorous look at the Country Music Awards which were held in Nashville, Tennessee, in November 2008.

Bryan Bedder/Getty Images

She paired her one-shoulder, lace dress with red lipstick and peep-toe heels.

In February 2009, she went for another glitzy gown at the Vanity Fair Oscar Party in West Hollywood, California.

Michael Buckner/Getty Images

Witherspoon finished off her outfit with a thick coating of black eyeliner.

In March 2009, she changed up her aesthetic when she wore a futuristic-looking minidress to the premiere of "Monsters Vs. Aliens" in Universal City, California.

Jason Merritt/Getty Images

The actor topped off her outfit with a pair of gray platform heels that had yellow accents.

In March 2010, Witherspoon wore a bubble minidress to the Vera Wang store launch in Los Angeles, California.

Jason Merritt/Getty Images

To complete this outfit, Witherspoon styled her hair to be pin straight.

In December 2010, Witherspoon went for a modern take on a vintage look when she was given a star on the Hollywood Walk of Fame in Hollywood, California.

Alberto E. Rodriguez/Getty Images

The actress matched her red heels to the miniature polka dots on her cap sleeve dress.

In October 2011, the actor layered a pantsuit over a lace top for ELLEs 18th Annual Women in Hollywood Tribute in Los Angeles, California.

Jason Merritt/Getty Images

Witherspoon used her green earrings and dark eyeliner to bring personality to her ensemble.

She wore another bubble dress with a floral pattern to the April 2011 premiere of "Water for Elephants" in New York City.

Jason Kempin/Getty Images

The actor glammed up this outfit with glitzy heels, shimmering earrings, and a ring of dark eyeliner.

Witherspoon wore a classic gown with a mermaid-style skirt to the Golden Globes in January 2012.

Frazer Harrison/Getty Images

She finished her outfit with tousledwaves, glitzy jewelry, red nail polish, and a touch of eyeliner.

In May 2012, Witherspoon wore a shimmery blue gown to an event at the Cannes Film Festival in Cannes, France.

Andreas Rentz/Getty Images

Witherspoon often gravitates toward glitzy gowns for red carpet events, and this occasion was no exception.

In February 2013, Witherspoon attended the Oscars wearing a strapless blue gown with a long train.

Michael Buckner/Getty Images

The actor softened this ensemble by styling her hair in large, romantic curls.

The star went for a more modern look at Benjamin Millepieds Los Angeles Dance Project Inaugural Benefit Gala in June 2013.

Alberto E. Rodriguez/Getty Images

Witherspoon's outfit had an especially edgy aesthetic because she deeply parted her hair to the side and wore a thick layer of eyeliner.

The star wore another mixed-material bubble dress to the March 2014 Film Independent Spirit Awards in Santa Monica, California.

Jason Merritt/Getty Images

For events and screenings, the actor often goes for floral, colorful dresses.

She wore another mixed-material gown to an October 2014 screening of "Wild" in London, England.

Tim P. Whitby/Getty Images

The actor topped off her outfit with her makeup staples: eyeliner, bronzer, and red lipstick.

The actor wore a pearl-emblazoned minidress with geometric sleeves to the Palm Springs International Film Festival Awards Gala in Palm Springs, California, in January 2015.

Frazer Harrison/Getty Images

She topped off her vintage-esqueoutfit with large curls, pink lipstick, and pointed-toe heels.

In February 2015, Witherspoon attended the Oscars in a modern, off-the shoulder gown.

Jason Merritt/Getty Images

She styled her hair in a sleek blowout and, of course, wore her signature eyeliner.

In October 2015, the actor wore another gown in a similar style when she was honored at the American Cinematheque Awards in Los Angeles, California.

Jason Merritt/Getty Images

She changed up her look by parting her sleek, straight hair to the side.

She went for a multicolored, patterned minidress for the December 2016 premiere of "Sign" in Los Angeles, California.

Frederick M. Brown/Getty Images

When she attends movie premieres, Witherspoon often wears an outfit that fits the movie's theme, as she did here.

In February 2016, she wore a strapless purple gown with a large train and an eye-catching bow.

Jason Merritt/Getty Images

The actor kept her hair and completed her outfit with bronzer, pink lipstick, and lots of eye makeup.

The actor wore a strapless black gown with a floral skirt and a thigh-high slit to the Tiffany & Co. Blue Book Gala in New York City in April 2016.

Jamie McCarthy/Getty Images

Witherspoon added some drama to her floral ensemble with red lipstick and severalglimmering accessories.

The actor wore another gown with a thigh-high slit to the January 2017 Golden Globes in Beverly Hills, California.

Frazer Harrison/Getty Images

She swept her hair into a side-parted updo and lined her eyes with dark makeup to finish the look.

The star changed things up when she donned a blazer minidress for the Emmy Awards in September 2017.

Dan Steinberg/Invision/AP

Witherspoon kept this outfit simple, pairing the dress with plain heels and statement earrings.

Also in September, she wore a one-shoulder dress with an unexpected fan-like adornment to a screening of "Home Again" in London, England.

Jeff Spicer/Getty Images

This was a more experimental look for Witherspoon.

She wore another one-shoulder black gown to the Golden Globes in January 2018.

Frederick M. Brown/Getty Images

Witherspoon completed her elegant outfit with eyeliner, soft pink lipstick, and glitzy jewelry.

The actor attended the January 2018 Screen Actors Guild Awards in Los Angeles, California, in a chevron, off-the-shoulder gown.

Jon Kopaloff/Getty Images

Witherspoon completed her glamorous ensemble with matching earrings, a touch of mascara, and glamorous curls.

One-shoulder dresses continued to be one of Witherspoons wardrobe staples. She wore one to the Hollywood, California, premiere of "A Wrinkle in Time" in February 2018.

Alberto E. Rodriguez/Getty Images

She amped up the glamorous outfit with dark eye makeup.

The actor wore a metallic floral dress with dramatic sleeves to a screening of "A Wrinkle in Time" held in New York City in March 2018.

Dimitrios Kambouris/Getty Images

The tea-length dress was a truly classic Witherspoon look, as it combined modern and vintage-inspired motifs.

In August 2018, Witherspoon wore a dress that appeared to be covered in black and white butterflies.

Jon Kopaloff/FilmMagic

She finished off her look for the launch event for "Shine On With Reese" in Hollywood, California, with soft waves, dark eye makeup, and statement-making earrings.

In October, Witherspoon attended the Los Angeles Dance Projects Annual Gala wearing a mixed-material dress.

Michael Tran/FilmMagic

She completed her outfit with a matching purse.

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42 photos that show how Reese Witherspoon's style has evolved over the years

In July 1999, Reese Witherspoon wore a grunge-meets-glam ensemble to "The Fear" premiere in Sydney, Australia.

At the Los Angeles, California, premiere of "Cruel Intentions" in February 1999, she paired a baby doll top with a maxi skirt.

In May 2000, she wore a strapless gray dress to the Sixth Annual Blockbuster Entertainment Awards in Los Angeles, California.

She fittingly wore an all-pink ensemble to the July 2001 premiere of "Legally Blonde" in Los Angeles, California.

Once again, Witherspoon mixed grunge and preppy pieces at the August 2002 The Teen Choice Awards in Los Angeles, California.

Witherspoon wore a mixed-material dress to the New York City premiere of "Sweet Home Alabama" in September 2002.

In June 2003, she wore a floral dress to the premiere of "Legally Blonde 2: Red, White & Blonde" in Southampton, New York.

In August 2004, Witherspoons outfit for a New York City screening of "Vanity Fair" really popped thanks to her dark brown hair.

In September 2005, the actress looked more like herself at the premiere of "Just Like Heaven" in Los Angeles, California.

Witherspoon wore a mermaid-style red dress to the November 2005 premiere of "Walk The Line" in New York City.

She went for another metallic look at the 2006 Golden Globes, which were held in Beverly Hills, California.

The actor wore an embellished, champagne-colored gown to the Oscars in 2006.

The actor changed things up for the January 2007 Golden Globes when she wore a bright yellow minidress with red heels.

The next month, she wore a tiered, purple gown to the Oscars in Hollywood, California.

She went for a decidedly glamorous look at the Country Music Awards which were held in Nashville, Tennessee, in November 2008.

In February 2009, she went for another glitzy gown at the Vanity Fair Oscar Party in West Hollywood, California.

In March 2009, she changed up her aesthetic when she wore a futuristic-looking minidress to the premiere of "Monsters Vs. Aliens" in Universal City, California.

In March 2010, Witherspoon wore a bubble minidress to the Vera Wang store launch in Los Angeles, California.

In December 2010, Witherspoon went for a modern take on a vintage look when she was given a star on the Hollywood Walk of Fame in Hollywood, California.

In October 2011, the actor layered a pantsuit over a lace top for ELLEs 18th Annual Women in Hollywood Tribute in Los Angeles, California.

She wore another bubble dress with a floral pattern to the April 2011 premiere of "Water for Elephants" in New York City.

Witherspoon wore a classic gown with a mermaid-style skirt to the Golden Globes in January 2012.

In May 2012, Witherspoon wore a shimmery blue gown to an event at the Cannes Film Festival in Cannes, France.

In February 2013, Witherspoon attended the Oscars wearing a strapless blue gown with a long train.

The star went for a more modern look at Benjamin Millepieds Los Angeles Dance Project Inaugural Benefit Gala in June 2013.

The star wore another mixed-material bubble dress to the March 2014 Film Independent Spirit Awards in Santa Monica, California.

She wore another mixed-material gown to an October 2014 screening of "Wild" in London, England.

The actor wore a pearl-emblazoned minidress with geometric sleeves to the Palm Springs International Film Festival Awards Gala in Palm Springs, California, in January 2015.

In February 2015, Witherspoon attended the Oscars in a modern, off-the shoulder gown.

In October 2015, the actor wore another gown in a similar style when she was honored at the American Cinematheque Awards in Los Angeles, California.

She went for a multicolored, patterned minidress for the December 2016 premiere of "Sign" in Los Angeles, California.

In February 2016, she wore a strapless purple gown with a large train and an eye-catching bow.

The actor wore a strapless black gown with a floral skirt and a thigh-high slit to the Tiffany & Co. Blue Book Gala in New York City in April 2016.

The actor wore another gown with a thigh-high slit to the January 2017 Golden Globes in Beverly Hills, California.

The star changed things up when she donned a blazer minidress for the Emmy Awards in September 2017.

Also in September, she wore a one-shoulder dress with an unexpected fan-like adornment to a screening of "Home Again" in London, England.

She wore another one-shoulder black gown to the Golden Globes in January 2018.

The actor attended the January 2018 Screen Actors Guild Awards in Los Angeles, California, in a chevron, off-the-shoulder gown.

One-shoulder dresses continued to be one of Witherspoons wardrobe staples. She wore one to the Hollywood, California, premiere of "A Wrinkle in Time" in February 2018.

The actor wore a metallic floral dress with dramatic sleeves to a screening of "A Wrinkle in Time" held in New York City in March 2018.

In August 2018, Witherspoon wore a dress that appeared to be covered in black and white butterflies.

In October, Witherspoon attended the Los Angeles Dance Projects Annual Gala wearing a mixed-material dress.