- Reese Witherspoon has been in the entertainment industry since the early ’90s.
- Witherspoon’s style has evolved a lot over the years.
- From combat boots to gowns and heels, here’s how the “Legally Blonde” star’s fashion has changed since 1996.
- Visit Insider’s homepage for more stories.
Since the early ‘90s, Reese Witherspoon has had a long, prolific career in the entertainment industry. Through dozens of red-carpet appearances for awards shows, movie, and TV show premieres, the actor has proved herself to be a true style icon.
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.
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.
Witherspoon quite literally tied her outfit together with a thin gold belt.
In May 2000, she wore a strapless grey dress to the Sixth Annual Blockbuster Entertainment Awards in Los Angeles, California.
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.
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.
The actor paired a Ralph Lauren logo top with a pair of flared corduroy pants.
Witherspoon wore a mixed-material dress to the New York City premiere of “Sweet Home Alabama” in September 2002.
Witherspoon completed her shimmery, colour-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.
She topped off her summery ensemble with strappy heels and bright, shimmery makeup.
In August 2004, Witherspoon’s outfit for a New York City screening of “Vanity Fair” really popped thanks to her dark brown hair.
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.
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.
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.
Witherspoon added a touch of colour with her rosy pink lipstick.
The actor wore an embellished, champagne-coloured gown to the Oscars in 2006.
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.
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.
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.
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.
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.
The actor topped off her outfit with a pair of grey platform heels that had yellow accents.
In March 2010, Witherspoon wore a bubble minidress to the Vera Wang store launch in Los Angeles, California.
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.
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 ELLE’s 18th Annual Women in Hollywood Tribute in Los Angeles, California.
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.
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.
She finished her outfit with tousled waves, glitzy jewellery, 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.
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.
The actor softened this ensemble by styling her hair in large, romantic curls.
The star went for a more modern look at Benjamin Millepied’s Los Angeles Dance Project Inaugural Benefit Gala in June 2013.
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.
For events and screenings, the actor often goes for floral, colourful dresses.
She wore another mixed-material gown to an October 2014 screening of “Wild” in London, England.
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.
She topped off her vintage-esque outfit with large curls, pink lipstick, and pointed-toe heels.
In February 2015, Witherspoon attended the Oscars in a modern, off-the shoulder gown.
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 honoured at the American Cinematheque Awards in Los Angeles, California.
She changed up her look by parting her sleek, straight hair to the side.
She went for a multicoloured, patterned minidress for the December 2016 premiere of “Sign” in Los Angeles, California.
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.
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.
Witherspoon added some drama to her floral ensemble with red lipstick and several glimmering accessories.
The actor wore another gown with a thigh-high slit to the January 2017 Golden Globes in Beverly Hills, California.
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.
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.
This was a more experimental look for Witherspoon.
She wore another one-shoulder black gown to the Golden Globes in January 2018.
Witherspoon completed her elegant outfit with eyeliner, soft pink lipstick, and glitzy jewellery.
The actor attended the January 2018 Screen Actors Guild Awards in Los Angeles, California, in a chevron, off-the-shoulder gown.
Witherspoon completed her glamorous ensemble with matching earrings, a touch of mascara, and glamorous curls.
One-shoulder dresses continued to be one of Witherspoon’s wardrobe staples. She wore one to the Hollywood, California, premiere of “A Wrinkle in Time” in February 2018.
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.
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.
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 2018, Witherspoon attended the Los Angeles Dance Project’s Annual Gala wearing a mixed-material dress.
She completed her outfit with a matching purse.
In May 2019, Witherspoon attended the season two premiere of “Big Little Lies” wearing a sleek dress with emerald jewellery.
She attended the event wearing an Elie Saab gown from the designer’s pre-fall 2019 collection.
In October 2019, she looked chic at the premiere of “The Morning Show.”
Witherspoon arrived at the premiere wearing a sparkly black-and-gold Celine gown with Christian Louboutin satin pumps.
In November 2019, Witherspoon wore different shades of green to a special screening of “The Morning Show.”
She arrived at the red carpet wearing a Brandon Maxwell satin minidress with a twill blazer jacket from the same designer.
In November 2019, Witherspoon suited up for the premiere of “Truth Be Told.”
The executive producer of the show looked so chic in a tailored black suit. She added a pop of colour with her Jennifer Meyer diamond and pink sapphire bezel earrings.
In November 2019, Witherspoon brought a bit of sparkle to the 53rd annual CMA Awards.
The actress wore a little black dress from Saint Laurent, matching pointed-toe pumps, and Nikos Koulis hoop earrings.
In December 2019, she wore navy blue to The Hollywood Reporter’s Women in Entertainment breakfast.
Witherspoon looked fabulous in a Michael Kors dress and Jimmy Choo pumps.
In January, Witherspoon arrived at the 2020 Golden Globes looking like a vision in white.
For the awards show, she wore a custom Roland Mouret gown, Tiffany & Co. jewellery, and Christian Louboutin sandals.
Witherspoon wore a monochromatic look to attend the 2019 New York Film Critics Circle Awards.
She wore an Andrew Gn embroidered floral dress, Chopard jewellery, and Saint Laurent pumps.
In January, Witherspoon wore a dazzling dress with a thigh-high slit to the 2020 SAG Awards.
She wore a Celine column dress with Harry Winston jewels.
In February, Witherspoon wore a sparkly look to the Vanity Fair 2020 Oscars after-party.
The actress and producer wore a Dolce & Gabbana dress with Forevermark jewellery. Witherspoon added a bit of edge with her spiked Christian Louboutin heels.
- Read more:
- How Reese Witherspoon became the queen of streaming, from ‘The Morning Show’ to ‘Little Fires Everywhere’
- Watch Reese Witherspoon’s 16-year-old son hilariously give her another TikTok lesson
- Beyoncé gave Reese Witherspoon a huge box full of Ivy Park clothing just a week after sending her a case of Jay-Z’s Champagne
- Reese Witherspoon shared a photo from her ‘girls night out’ with her 20-year-old lookalike daughter
Business Insider Emails & Alerts
Site highlights each day to your inbox.