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Serena Williams was always en vogue

The tennis star broke style barriers on and off the court

It was fitting for Serena Williams to say goodbye to tennis in the pages of a fashion magazine. Williams announced her retirement from the sport in the September issue of Vogue — a prestigious spot that volleyed Williams into her next era: fashion mogul.

It was a full circle moment for the decorated athlete, who has starred as one of editor-in-chief Anna Wintour’s cover girls three times. Before the September 2022 issue, Williams was on the cover of the February 2018 issue of Vogue with her daughter, then-4-month-old Alexis Olympia Ohanian Jr. And she appeared on the April 2015 issue for her first solo cover. At the very end of that story, Williams dropped a little nugget: When she finally decided to retire, she hoped to “expand her interest in fashion beyond her current clothing line on the Home Shopping Network into something more high-end.”

In her September 2022 letter from the editor, Wintour wrote: “Serena has traveled between the worlds of sport and fashion as naturally as anyone I could think of — and her brilliance has always been tied to her fearlessness, in the evident joy she takes in pushing boundaries and trying something new.”

In 1998, Williams played in the Australian Open for the first time. She would lose to her sister, Venus, but as The New York Times reported then, “What you saw was something for the future.”

They were right, in more ways than one.

That same year, photographer Annie Leibovitz shot Williams and Venus for Vogue wearing black-and-white striped Carolina Herrera dresses with their signature beads in their hair.

“This was my first shoot for Vogue, and I did it with Venus in this picture, and you can see we have our hair in — we were really young — we still had our beads,” she recalled in Vogue’s Life in Looks. “We still had our youth. It was such an amazing moment. I just remember being so excited to shoot for Vogue.

Williams told the magazine that wearing the beads gave her a sense of freedom. 

In the fashion world, having your portrait taken by Leibovitz is a big deal. She’s captured some of the world’s biggest celebrities for high-society’s most exclusive publications, such as Vogue and Vanity Fair. For the Williams sisters to be photographed so early in their careers wearing beautiful dresses with beads in their hair in a magazine that upholds a beauty standard few people, including the Williams sisters, could meet, was unheard of at the time.

“I still have the beads, and you can start to see that I’m wearing a ton of accessories,” Williams told Vogue, while looking at a photo of herself at the 1999 US Open. “My mom was actually doing my hair back then. I did the beads though, I felt like my freedom was being able to pick out my beads.”

For the Williams sisters, wearing their hair braided with beads was part of being a regular Black girl. But it also served as a symbol to the world that they were here to take up space and make noise.

From the beginning of Williams’ career, her appearance was freighted. She and her sister were caricatured with exaggerated bodies and features. Throughout her career Williams was a rare instance of representation in an elite white space, and she was constantly a target of criticism from the tennis establishment because of it.

She credits her 2003 shoot with Vogue as helping her to feel confident in her body. She wasn’t photographed wearing her tennis gear, opting to pose poolside in a white bikini with her hair wet as if she had just emerged from the water. “I wasn’t the average athlete,” Williams said in Vogue’s Life in Looks video series. “I was this crazy insane athlete who had crazy curves and still was moving just as fast as anyone else.”

And it wasn’t an average shoot for Vogue, either. Williams’ curves weren’t just a departure for women in sports, they were a departure from the waiflike body type typically presented wearing expensive clothing in the fashion magazine.

Williams’ love affair with fashion began at home with her mother, who used to make all of her and Venus’s clothes from old Vogue clothing patterns. Williams eventually would study fashion at the Art Institute of Fort Lauderdale from 2000 to 2003.

Serena Williams wears a Puma soccer-inspired outfit during a match at the French Open on May 20, 2002, in Paris.

FRANCOIS GUILLOT/AFP via Getty Images

At the 2002 French Open, Williams wore a Puma ensemble inspired by a Cameroon soccer uniform: knee-high yellow socks, sneakers resembling cleats (without the spikes) and a green dress with yellow trim up the side. Her blond braids were pulled off her face into a high ponytail with a red, green and yellow headband.

Because of the game’s elitist foundation, any player’s departure from wearing tennis whites was considered controversial. Andre Agassi famously boycotted Wimbledon from 1988 to 1990 because he refused to wear white. The idea that a tennis player should wear white goes back to the Victorian era, when it was believed white clothing hid sweat better. That, and because only upper-class people were able to keep their white clothing clean. So showing up to play in highlighter yellow would have been frowned upon 20 years ago.

“I remember being so nervous and I was like I can’t believe I’m going to go out on the court like this,” she recalled. “I actually only wore this outfit two times because it really was all about the fashion, and less about the tennis, and I was like, no, I want to do well. I want to win. This was such an iconic moment but of course at the time, I didn’t know that.” 

Though she’d experimented with her on-court style, it wasn’t until Williams began working with Nike that she came into her own. She wanted, as she told Vogue, “pizzazz.” 

The first look she created with Nike was a breathable and stretchy pleated denim skirt she wore with custom-designed knee-high boots that zipped off to reveal the sneakers she could actually play in at the 2004 US Open. Williams saw Andre Agassi compete in a pair of jean shorts and told Nike she wanted to try a similar look for herself — kicking off a series of looks that pushed boundaries.

Off the court, Williams was coming into her own as a fashionista who understands functional clothing can be on-trend. In 2014, Williams debuted the Serena Williams Signature Statement Runway Collection during New York Fashion Week. She wore a black waxy-leather short-sleeved cropped top and matching leather tennis skirt that she designed herself, along with black Alaïa heels. 

The 22-piece collection consisted of leggings, vests, cardigans, and blouses priced under $100 and aimed to allow the wearer to go from work to play (and maybe hit the gym in between). At the time, athleisure was still a new trend, and not a very popular one. Tighter body-conscious silhouettes and platform high heels were the go-to look for trendy women.

Williams’ collection was also groundbreaking in that it was available through HSN immediately after the pieces debuted on the runway — one of the earliest examples of “see now, buy now” collections allowing consumers to shop for the season the collection is shown for. It would be another three years before designers such as Ralph Lauren, Tom Ford, and Tommy Hilfiger would do the same.

In May 2018, Williams launched a new clothing line, with similar style pieces as her Signature Statement Runway Collection, simply called Serena Williams. It was independent of her HSN line and is sold directly to consumers on her own branded website. 

A year later, in November 2019, Williams launched her first jewelry line, Serena Williams Jewelry, an expansion of her clothing collection. 

“I love wearing jewelry when I play,” she said during the press preview for the launch in New York. “I used to wear the craziest earrings. I have to accessorize when I’m out there because most times, that’s only when people see my hands when I’m out there.”

During this time Williams was also stepping out on red carpets more, including at fashion’s biggest night: the Met Gala.  

Now cemented among the fashionable set, Williams attended the 2017 Met Gala pregnant in a custom-made emerald green Atelier Versace halter-style gown with vertical beaded accents and a long train. 

A few months later, she wed Alexis Ohanian wearing a strapless Alexander McQueen ball gown, cape and veil attached to her chignon. For the reception, she changed into a beaded and feathered Versace gown. Her third look was also by Versace, a beaded mini dress with a feather skirt.

Her love affair with Donatella Versace’s work continued when she wore another Versace look to witness her friend Meghan Markle wed Prince Harry. This time, she wore a long-sleeved pink shift-dress.

Williams tapped Versace again for her appearance at the 2019 Met Gala, opting for a voluminous yellow Atelier Versace gown with pink floral appliques floating on its hem up to its billowing sleeves. But the real statement was the highlighter yellow Off-White x Nike Air Force 1 Low Volt sneakers her friend Virgil Abloh got for her the night before the gala.

The sneakers marked her friendship with Abloh, whom she met through Nike. In 2018, Williams took the court in the French Open in the now-infamous full body black catsuit that helped prevent blood clots after a difficult delivery and postpartum complications. The suit, which Abloh designed, spawned all sorts of microaggressions, and was even banned by the French Tennis Federation. Williams returned to the US Open the following year in a one-shoulder dress Abloh designed with the Nike swoosh and the word logo — his signature air quotes were around the word logo — emblazoned on the chest with a tulle skirt.

Nike and Abloh’s Off-White collaborated on The Queen Collection available for fans, inspired by pieces Williams wore at the US Open, including two dresses, a bomber jacket, a bag, and limited editions of The 10: Nike Air Max 97 and The 10: Nike Blazer Mid SW sneakers.

“I was a kid that Michael Jordan was superman to me,” Abloh said at Westside Tennis Club in Queens, during a conversation to celebrate the collection with curator and author Kimberly Drew and Williams in 2018. “Venus and Serena were superwomen. You know you’re a kid in school, you listen to your favorite music artist but sports was where you saw people defeat odds and saw larger-than-life things happen in a game of champs.”

Abloh continued: “This is the perfect position for me to be able to translate icons but also make something that’s attainable that you can sort of feel linked to these great achievements. I like to make things that people can see themselves in so that they can feel like they are tied to it.”

As Williams’ star power was cemented, so was her place in fashion. 

For the first time, Williams walked a designer runway that wasn’t her own. On the first day of Paris Fashion Week, she walked in Off-White’s Fall 2022’s show wearing a sheer printed long-sleeve turtleneck and matching pants under a navy halter dress from Abloh’s final collection. He died from cancer in November 2021. Williams told Vogue she walked in the show to honor her friend as a favor to Abloh’s wife.

“[Abloh] was an amazing designer, doing the things that he did in such a big way,” she said. “Designing for Nike, designing his own collection with Off-White, designing for Louis Vuitton. It’s stuff that movies are literally made out of.” 

In March, Williams announced Serena Ventures, an early-stage venture capital firm focusing on founders with “diverse points of view” that raised $111 million. She also sits on the board of Poshmark, an e-commerce marketplace specializing in selling secondhand fashion and home goods.

Williams’ love of fashion has always gone hand in hand with her tennis career and it’s clear she’s not finished making her mark in the industry just yet.

In her final grand slam of a fashion statement, Williams would play the first round of the 2022 US Open in a Nike dress inspired by a figure-skater’s performance outfit, complete with a six-layer skirt to memorialize Williams’ six US Open championships.

Channing Hargrove is a senior writer at Andscape covering fashion. That’s easier than admitting how strongly she identifies with the lyrics “Single Black female addicted to retail.”