Southern Charm Meets Hollywood Glam: Reese Witherspoon’s Red Carpet Style Evolution

Since entering the entertainment industry over 30 years ago, Reese Witherspoon has been a fixture on screen and on the red carpet. She appeared in her first film, 1991’s The Man in the Moon, at the age of 14, but her big break came in 1999, when she starred in Cruel Intentions and Election. She cemented her Hollywood status with her now-iconic turn as Elle Woods in Legally Blonde in 2001.

In the ‘90s, Witherspoon’s red carpet looks embraced the fashion mentality of the era—think leather jackets, slip dresses and combat boots, but with a feminine, subtly preppy touch that hinted at her Southern roots. Over two decades before Margot Robbie’s Barbie press tour, Witherspoon took to method dressing with a slew of all-pink looks as she promoted Legally Blonde.   

As Witherspoon’s star power grew, so did her confidence on the red carpet. By the time she won an Oscar for her portrayal of June Carter in 2005’s Walk the Line, the actress had settled into her signature aesthetic: feminine, old Hollywood gowns with a dash of Americana. 

Witherspoon began working with stylist Leslie Fremar around 2010, staying true to her preppy roots—including plenty of bows—while also adopting a more sophisticated, mature take on the red carpet, characterized by bold colors and sparkling embellishments. In 2015, Witherspoon was named People’s best-dressed star; the same year, she founded Draper James, a Southern-inspired, preppy lifestyle brand. 

Since 2023, Witherspoon has worked with celebrity stylist Petra Flannery (her other clients include Zoe Saldaña and Emma Stone), and while the actress has remained loyal to her tried-and-true style, she’s also showcased a more tailored, polished wardrobe, with a preference for ensembles that make a statement through silhouette, not pattern. Though Witherspoon once said that she rarely wears all black because of her Southern roots, she began experimenting with the dark hue—a distinct change from her usual favored bright colors—more on the red carpet as her look matured. Unlike many other A-listers, Witherspoon hasn’t ever formally signed on as a brand ambassador to a luxury fashion house, and as such, has been able to experiment with different designers throughout her career, instead of sticking with one particular label during red carpet runs. 

From her very first red carpets to her many Academy Awards gowns, see Reese Witherspoon’s red carpet  style evolution over the years.

The Man in the Moon Premiere

• October 2, 1991

For the premiere of her film debut, The Man in the Moon, in Los Angeles, a 14-year-old Witherspoon wore a fittingly youthful and playful daisy top, a black skirt and cowboy boots. 

Fear Premiere

• April 1, 1996

Celebrating the premiere of Fear, Witherspoon arrived in a simple, long maroon dress and a navy cardigan with sequin embellishments. 

Special screening of The People vs. Larry Flynt

• October 13, 1996

In true ‘90s fashion, Witherspoon wore a black crop top and a low-waisted black skirt with a thick belt to a screening of The People vs. Larry Flynt.

58th Annual Golden Globe Awards

• January 21, 2001

For her first Golden Globes appearance in the early aughts, Witherspoon wore a black cocktail dress with a large flower detail, accessorizing with a triple loop of black pearls. She completed the look with a Veronica Lake-inspired hairstyle.

Legally Blonde Premiere

• July 13, 2001

At the premiere of Legally Blonde, Witherspoon fully embraced method dressing in a hot pink dress with black mesh overlay, in a clear nod to her on-screen persona, Elle Woods. 

The 74th Academy Awards

• March 24, 2002

At the 2002 Academy Awards, Witherspoon once again channeled Old Hollywood glamour in a black lace Valentino gown with detailed beading and sheer sleeves. From her softly waved hairstyle to her red lip, she embraced a 1920s-inspired look.

Legally Blonde 2 Premiere

• July 2, 2003

Pregnant with her second child, Witherspoon wore a simple white dress with a red velvet ribbon and matching red shoes to the Legally Blonde 2 premiere in London, which she attended with her then-husband, Ryan Phillippe.

63rd Golden Globe Awards

• January 16, 2006

Witherspoon arrived at the 2006 Golden Globes in a metallic-trimmed, cream-colored Chanel cocktail dress. While she was reportedly told this was a vintage piece from the fashion house, it turned out it had actually been worn by Kirsten Dunst to an awards after-party just three years prior. Despite this fashion upset, Witherspoon still came out on top that evening, as she won the best actress award for her portrayal of June Carter in Walk the Line.

The 78th Academy Awards

• March 5, 2006

The first-time nominee brought a timeless elegance to the 2006 Academy Awards, arriving in a champagne-colored, delicately beaded floor-length Dior gown. Witherspoon’s embellished gown proved good luck, as she won the Best Actress Oscar for Walk the Line.

64th Golden Globe Awards

• January 15, 2007

Highlighting Witherspoon’s love of color, Leslie Fremar styled her in a yellow Nina Ricci cocktail dress with an ombre pattern for the 2007 Golden Globes. Red Brian Atwood heels contrasted with the sunny hue of her frock. She kept her hair straight, and debuted her new bangs.

The 79th Academy Awards

• February 25, 2007

At the Academy Awards the following month, Witherspoon chose another Nina Ricci dress, this time in a purple ombré with feminine ruffles.

2008 Four Christmases Premiere

• November 26, 2008

At the Four Christmases premiere, Witherspoon wore a mid-length, navy strapless dress with gold detailing. While Witherspoon doesn’t often favor specific designers, this dress marked her third time wearing Nina Ricci in one year.

2009 Vanity Fair Oscar Party

• February 22, 2009

Witherspoon experimented with silhouettes in a black and blue Rodarte dress, which featured draping throughout and beaded accents between the sections.

2009 Monsters vs Aliens Premiere

• March 22, 2009

In keeping with the theme of her new animated film, Monsters vs. Aliens, Witherspoon arrived at the premiere in a futuristic silver and green short-sleeved Rodarte mini dress.

The 83rd Academy Awards

• February 27, 2011

Witherspoon exuded ‘60s mod elegance at the 2011 Academy Awards, wearing an Armani Privé fitted black gown with a contrasting white bandeau detail. Her updo showed off her dangling Neil Lane emerald earrings.

2011 MTV Movie Awards

• June 5, 2011

Opting for a fun, playful look befitting the MTV Movie Awards’ atmosphere, Witherspoon showed up to the red carpet in a Zac Posen cheetah-print mini with a sweetheart neckline. Letting the dress speak for itself, she accessorized with subtle nude shoes and minimal accessories.

70th Golden Globe Awards

• January 15, 2012

For the 2012 Golden Globes, Witherspoon chose another Zac Posen dress, but in a decidedly more glamorous silhouette for the formal event. Never one to shy away from bold colors, Witherspoon wore a red satin bustier gown with a mermaid-style hem from the designer’s 2012 Pre-Fall collection.

2012 Cannes Film Festival

• May 26, 2012

Witherspoon dazzled at the 2012 Cannes Film Festival, showing off her baby bump in a navy silk chiffon Versace gown that was covered in Swarovski crystals.

2013 Toronto International Film Festival

• September 8, 2013

At the 2013 Toronto International Film Festival, Witherspoon went for a more casual look in a patterned Jason Wu resort dress with a cutout neckline, paired with bright green pumps that stood out against the black-and-grey frock.

2014 Vanity Fair Oscar Party

• March 2, 2014

For the 2014 Vanity Fair Oscar Party, Witherspoon kept up her streak of patterned looks in a Hugo Boss dress, with a plunge neckline and a half-paillette-embroidered skirt.

2014 Met Gala

• May 5, 2014

For her first Met Gala appearance, Reese Witherspoon wore a hot pink, structured Stella McCartney gown. The event’s theme, “Charles James: Beyond Fashion,” celebrated the sculpted ballgowns and looks designed by Charles James.

72nd Golden Globe Awards

• January 11, 2015

Nominated for her role in Wild, Witherspoon sparkled at the 2015 Golden Globes in a shimmering, strapless Calvin Klein column dress.

2015 Met Gala

• May 4, 2015

Witherspoon chose a simple, bright red gown with a square neckline for the 2015 Met Gala, “China: Through the Looking Glass.” She paired the dress with matching red heels and diamond jewelry. 

The 88th Academy Awards

• February 28, 2016

For the 2016 Academy Awards, Witherspoon selected a purple Nina Ricci gown with a corset top and a structured ruffled bodice. It was somewhat reminiscent of another purple Nina Ricci dress she wore to the awards show nearly a decade prior. 

74th Golden Globe Awards

• January 8, 2017

Witherspoon lit up the 2017 Golden Globes in a sunshine-yellow strapless gown by Versace, featuring a sweetheart neckline and a high slit. She finished the look with a gold diamond choker, letting the gown take center stage. 

2017 Met Gala

• May 1, 2017

Witherspoon embraced the 2017 Met Gala theme—Rei Kawakubo/Comme des Garçons: Art of the In-Between—in a custom Thierry Mugler blue and black dress with a structured one-shoulder, textured top. The theme honored the work of Japanese designer Rei Kawakubo, who pushed fashion boundaries with texture, structure and other elements.

The 69th Primetime Emmy Awards

• September 17, 2017

Bringing a chic twist on suiting to the Emmy Awards, Witherspoon, nominated for her work on Big Little Lies, wore a sharp Stella McCartney teal satin blazer dress. To complete the upscale preppy look, she added a bold red lip and black stilettos. 

75th Golden Globe Awards

• January 7, 2018

At the 75th Golden Globe Awards, Witherspoon embodied sleek minimalism in a Zac Posen one-shoulder black gown with a sweeping train. The look highlighted the nominee’s polished and timeless style. 

2019 The Morning Show Premiere

• October 28, 2019

Witherspoon amped up the glamour in a strapless black-and-gold dress by Celine for a bold, glitzy look at the premiere of The Morning Show. Witherspoon wore her short hair slicked back, with heavy eyeliner and a pink lip.

77th Golden Globe Awards

• January 5, 2020

At the 2020 Golden Globes, Witherspoon scaled back on the embellishments and opted for a more understated, clean look in a Roland Mouret white one-shoulder gown. She styled the dress with straight, tucked-back hair and delicate jewelry. 

The 93rd Academy Awards

• April 25, 2021

Wearing a red pleated off-the-shoulder gown from Dior’s Fall 2021 collection, Witherspoon wasn’t afraid to stand out at the 93rd Academy Awards. A slim black belt offset the flowing silhouette of the dress.  

The 28th Annual Screen Actors Guild Awards

• February 27, 2022

At the 2022 SAG Awards, Witherspoon debuted her first Schiaparelli look: a black strapless gown with a sweeping blue sash and a neckline that curved at the edges, giving the gown a distinctive shape.

74th Primetime Emmy Awards

• September 12, 2022

Displaying her love for bold glamour, Witherspoon chose a dazzling black and teal sequin dress from Armani Privé’s fall collection. The gown sparkled enough on its own, and the actress accessorized with a teal diamond necklace, matching earrings and strappy black sandals, with straight and simple hair that allowed the dress to shimmer on its own.

2023 Your Place or Mine Premiere

• February 2, 2023

Known for bringing a preppy, southern look to the red carpet, Witherspoon stood out at the 2023 Your Place or Mine premiere in a turquoise Valentino peplum dress.  

81st Golden Globe Awards

• January 7, 2024

Witherspoon arrived at the 2024 Golden Globes in a Monique Lhuillier dress that showcased her signature feminine, preppy style—a classic, fitted silhouette with pink off-the-shoulder details.

31st Screen Actors Guild Awards

• February 24, 2024

Staying true to her favored red carpet aesthetic, Witherspoon opted for an Elie Saab red couture dress with a structured top and matching shoes at the 2024 SAG Awards.

76th Primetime Emmy Awards

• September 15, 2024

Styled by Petra Flannery, Witherspoon continued her string of classic, glamorous red carpet gowns in an elegant, black Dior number with gold details and a tulle skirt.

2025 You’re Cordially Invited Premiere

• January 28, 2025

Sticking with her go-to preppy style, Witherspoon brought back the peplum look at the premiere of You’re Cordially Invited in a black Louis Vuitton skirt and jacket combo.

Season 4 premiere of The Morning Show

• September 9, 2025

In celebration of the season four premiere of The Morning Show, Witherspoon matched her co-star, Jennifer Aniston, in a black asymmetrical David Koma dress, featuring a large statement bow at the hip.