A look back at how Serena Williams's style broke down barriers

Over a long and storied career, the 23-time Grand Slam winner used fashion to challenge entrenched sexism and racism in tennis

Serena Williams never shied away from boundary-breaking looks, on or off the court. Photo: USA Today Sports, TPX

From glossy magazine covers to generation-defining on-court styles, Serena Williams took a bow at the US Open on Friday, having rewritten the fashion playbook for female athletes while building an empire of her own.

The 23-time Grand Slam winner chose Vogue to announce she was "evolving away from tennis," before taking to the court in her bedazzling Nike sneakers at the US Open this week, under the watchful eyes of the magazine's head, Anna Wintour.

The fiercely competitive queen of Queens put on a gritty performance in what is widely expected to be her final tournament, losing in the third round 7-5 6-7 (4) 6-1 to Ajla Tomljanovic, with her legacy as a cultural phenomenon firmly in place.

Serena and her sister Venus faced criticism in the 1990s for wearing their hair in beaded braids in competition, as they rose through a predominantly white sport. Getty

"Style and sport have always been closely intertwined, but no athlete embraced the power of fashion like Serena Williams," Katie Abel, executive editor of Footwear News, told Reuters.

"She’s never shied away from boundary-breaking looks, on or off the court, and always knows how to send a message, even if it’s controversial."

She famously competed in Flushing Meadows in a denim skirt in 2004 and ruffled feathers at Roland-Garros in 2018, when she wore a black catsuit to keep her circulation going after developing blood clots in the days after giving birth.

Williams returns to Jennifer Capriati during the US Open on September 7, 2004, wearing a controversial denim skirt. Getty

After organisers said they would ban the catsuit from their clay courts, Williams' supporters cried foul. Williams quipped to the Associated Press: "When it comes to fashion, you don’t want to be a repeat offender."

The moment showed she could harness fashion to disrupt the status quo, said Katie Lebel, a researcher of gender equity in sport and assistant professor at the University of Guelph.

"Sexism has been pretty pervasive when it comes to women’s clothing... The expectations around what women athletes should look like that been particularly steeped in that," she said.

"Enter Serena and she pushed back against all this. I think she really rethought [the] uniform standards for women in tennis."

Williams wore a black catsuit in 2018 to keep her circulation going after developing blood clots in the days after giving birth, a move that placed women's health in the spotlight. AFP

Serena and her sister Venus brought black style to the overwhelmingly white sport when they first took the court as professionals in the 1990s, facing criticism for wearing beaded braids in competition.

Williams wore the style when she won her inaugural Grand Slam in New York. Photos of daughter Olympia in identical plaits in the stands at Flushing Meadows this year were an instant sensation.

"From the moment Serena and her sister Venus stepped onto the court in their signature braids... they have been role models for black women and aspiring female athletes everywhere," said Abel.

Glam Slam

Williams's friendship with late Louis Vuitton artistic director Virgil Abloh resulted in one of her most memorable US Open ensembles, a ballerina-inspired Nike kit in 2018, when she got tantalisingly close to clinching a record-equalling 24th major title but came up short in the final.

While her run at the US Open is over, her work in New York has just begun, with a "Glam Slam" preview of new looks from her S by Serena brand planned for September 12 to coincide with New York Fashion Week.

And her retirement from competitive sport is expected to have little to no impact on her brand value — with Nike planning to continue its partnership with the player, aged 40.

"Williams may be retiring from tennis, but I’m guessing her influence on fashion is just getting started. Without her gruelling training schedule, I’d think she would have even more time and energy to focus on this category," said W Magazine fashion director Nora Milch.

Williams waves to fans as she arrives prior to the Balmain autumn/winter 2022-2023 collection fashion show during the Paris Womenswear Fashion Week. AFP

A bona fide fashion tycoon off the court, Serena was named to the board of shopping app Poshmark in 2019, opening her own closet alongside pieces of Olympia's to customers on the fashion marketplace.

Manish Chandra, Poshmark founder and chief executive, said Williams has inspired several other female entrepreneurs to sell on the app by way of her unique voice and perspective.

"As a champion of female empowerment, Serena always leads with love and helps to ensure that our Poshmark community is front and centre in everything we do," Chandra said.

"Her achievements and vision across the worlds of business, fashion and entrepreneurship made her a perfect fit for our board... She leads with humility, kindness and authenticity."

Scroll through images of Serena Williams's fashion evolution below

Venus and Serena Williams, wearing a green T-shirt, with former president Ronald Reagan at a tennis camp in Florida in 1990. AFP

Serena Williams, in black shorts and a green check swimsuit, in Key Biscayne, Florida in March 1998. Getty Images

Serena Williams, wearing a grey coat, during the Chase Championships in New York City, New York on November 16, 1998. Allsport

Serena Williams, in a silver dress, and Venus Williams arrive to attend the Laureus World Sports Awards in Monte Carlo, Monaco on May 25, 2000. Reuters

Serena Williams, in a pink dress of her own design, attends the 2003 ESPY Awards at the Kodak Theatre July 16, 2003 in Hollywood, California. AFP

Venus Williams and Serena Williams, in a black dress, attend the 2003 MTV Video Music Awards at Radio City Music Hall on August 28, 2003 in New York City. AFP

Serena Williams, in a purple satin gown, attends the 2004 Met Gala in New York City on April 26, 2004. AFP

Serena Williams, in an orange mini dress, attends the 12th Annual ESPY Awards held at the Kodak Theatre on July 14, 2004 in Hollywood, California. AFP

Serena Williams, in a pink patterned dress, attends the 'Catwoman' premiere at the ArcLight Theatre on July 19, 2004 in Hollywood, California. AFP

Serena Williams, in a white dress with floral detail, attends the Coty 100th Anniversary Party at the American Museum of Natural History on September 12, 2004, in New York City. AFP

Serena Williams, in a blush pink dress, attends the 'After The Sunset' premiere at Grauman's Chinese Theatre on November 4, 2004 in Hollywood, California. AFP

Serena Williams, in a pink halterneck dress, attends a preview gala dinner for the Metropolitan Museum's Wild: Fashion Untamed exhibition at the Metropolitan Museum of Art on December 6, 2004, in New York City. AFP

Serena Williams, in a white floral prom dress, attends the White House Correspondents dinner at the Washington Hilton Hotel on April 30, 2005, in Washington, DC. AFP

Serena Williams, in a yellow blouse, arrives at the 'Sky High' premiere at the El Capitan Theatre on July 24, 2005 in Hollywood, California. AFP

Serena Williams, in a belted white shirt, attends the 'ATL' premiere at Grauman's Chinese Theatre on March 30, 2006 in Hollywood, California. AFP

Serena Williams, in a taupe blouse, attends the Sony Ericsson players party at Opium nightclub March 26, 2008 in Miami Beach, Florida. AFP

Serena Williams, in white Calvin Klein, attends the label's spring/summer 2009 show during Mercedes-Benz Fashion Week on September 11, 2008 in New York City. AFP

Serena Williams, in a leopard print dress, arrives at the players kick-off party at Liv club, Miami on March 25, 2009. AFP

Serena Williams, in a teal Roberto Cavalli gown, arrives at the 2009 ESPY Awards held at Nokia Theatre LA Live on July 15, 2009 in Los Angeles, California. AFP

Serena Williams, in a red one-shouldered gown, attends the Glamour Magazine 2009 Women of The Year event at Carnegie Hall on November 9, 2009 in New York City. AFP

Serena Williams, in a black dress, attends the 18th Annual Elton John Aids Foundation Academy Award Party at Pacific Design Centre on March 7, 2010 in West Hollywood, California. AFP

Serena Williams, in a nude Burberry dress, arrives at the Burberry Body event on October 26, 2011 in Beverly Hills, California. AFP

Serena Williams, in a pink belted dress, arrives at Nickelodeon's 2011 TeenNick Halo Awards held at the Hollywood Palladium on October 26, 2011 in Hollywood, California. AFP

Serena Williams, in a blue and black dress, attends 'Think Like A Man' premiere in Hollywood, California on February 9, 2012. AFP

Serena Williams, in red trousers with a white top and black cardigan, attends the 13th Annual BNP Paribas Taste of Tennis benefit at the W New York Hotel on August 23, 2012 in New York City. AFP

Serena Williams, in a blue dress, attends the 14th Annual BNP Paribas Taste Of Tennis at W New York Hotel on August 22, 2013 in New York City. AFP

Serena Williams, in a navy blue gown, attends the 11th annual CFDA Vogue Fashion Fund Awards at Spring Studios on November 3, 2014 in New York City. AFP

Serena Williams, in a red Ines Di Santo gown, arrives for the Vanity Fair Oscar After-Party following the 87th annual Academy Awards ceremony in Hollywood, California on February 22, 2015. EPA

Serena Williams, in off-white Galia Lahav, arrives for the Vanity Fair Oscars After-Party following the 88th annual Academy Awards ceremony in Hollywood, California on February 28, 2016. EPA

Serena Williams, in a metallic LaQuan Smith gown, attends the premiere of 'Serena' on June 13, 2016 in New York City. AFP

Serena Williams, in a white two-piece with a pink bralette, attends the Berlei Sports Bras Launch At Macy's With Serena Williams on August 25, 2016 in New York City. AFP

Serena Williams, in a sheer floral gown, attends the Serena Williams Signature Statement Collection By HSN on September 12, 2016, in New York City. AFP

Serena Williams, in a black dress, attends the Charity Gala Dinner for the Novak Djokovic Foundation on September 20, 2016 in Milan. AFP

Serena Williams, in a white jacket with a feathered skirt, attends an Audemars Piguet event on November 29, 2016 in Miami Beach, Florida. AFP

Serena Williams, in an emerald green Versace gown, attends the 2017 Met Gala at the Metropolitan Museum of Art on May 1, 2017 in New York City. AFP

Serena Williams, in a navy lace dress, attends the launch of the Burberry DK88 Bag hosted by Christopher Bailey at Burberry Soho on May 2, 2017 in New York City. AFP

Serena Williams, in a black and gold dress, attends 'Glamour' magazine's 2017 Women of The Year Awards at Kings Theatre on November 13, 2017 in Brooklyn, New York. AFP

Serena Williams, in a white Tom Ford dress with sequinned sleeves, attends the premiere of 'Being Serena' at Time Warner Centre on April 25, 2018 in New York City. AFP

Serena Williams, in a dusky pink Versace dress, and Alexis Ohanian arrive for the royal wedding ceremony of Britain's Prince Harry and Meghan Markle at St George's Chapel in Windsor Castle, in Windsor on May 19, 2018. EPA

Serena Williams, in a leopard-print dress, attends the 5th Annual Imagine Ball Honouring Serena Williams at The Peppermint Club on September 23, 2018 in Los Angeles, California. AFP

Serena Williams, in a metallic Vera Wang dress, attends the 2018 Brand Genius Awards at Cipriani 25 Broadway on November 7, 2018 in New York City. AFP

Serena Williams, in jeans and a denim jacket, attends the Teen Vogue Summit at 72andSunny on December 1, 2018 in Los Angeles, California. AFP

Serena Williams, in a black and red Armani Prive gown, attends the 91st Annual Academy Awards at Hollywood and Highland on February 24, 2019 in Hollywood, California. AFP

Serena Williams, in a blue and black Giambattista Valli gown, attends the 2019 Vanity Fair Oscar Party in Beverly Hills on February 24, 2019. AFP

Serena Williams, in a yellow floral Versace gown, attends the 2019 Met Gala at the Metropolitan Museum of Art on May 6, 2019 in New York City. AFP

Serena Williams, in a white top and fawn skirt, attends the Sports Illustrated Fashionable 50 at The Sunset Room on July 18, 2019 in Los Angeles, California. AFP

Serena Williams, in a white slip dress, attends the Game Changers New York premiere at Regal Battery Park 11 on September 9, 2019 in New York City. AFP

Serena Williams, in an orange dress with a Burberry shawl, attends a charity event at Harriet's Rooftop in West Hollywood on October 3, 2019. AFP

Serena Williams, in a silver one-piece and feathered cape by Gucci, attends the 2021 Met Gala at the Metropolitan Museum of Art in New York City on September 13, 2021. AFP

Serena Williams, wearing black Gucci, attends the 10th Annual Lacma Art and Film Gala at Los Angeles County Museum of Art on November 06, 2021. AFP

Serena Williams, in black sportswear, attends Cloud9 Champion's Day on November 9, 2021 in Los Angeles, California. AFP

Serena Williams, in a black embellished David Koma leotard, attends the premiere of 'King Richard' at TCL Chinese Theatre on November 14, 2021 in Hollywood, California. AFP