This story appears in the July 29–August 5, 2019, issue of Sports Illustrated, which features the 2019 Fashionable 50 list, honoring the most stylish athletes in sports right now. For more great storytelling and in-depth analysis, subscribe to the magazine—and get up to 94% off the cover price. Click here for more.
Serena Williams was fashionably late. Then officially late. Then worryingly late. This wasn’t diva behavior or another celebrity operating on a clock of her own. This was something more significant. As the hours ticked by inside a sweeping studio space in a business park on the outskirts of London, Serena sat in a doctor’s office just a few miles away, waiting for information about her health.
After a routine practice session on the grass earlier that morning, she hadn’t felt well, and with Wimbledon just days away, the 23-time Grand Slam champion and mother of 22-month-old Alexis Olympia didn’t want to take a chance.
Following a quick evaluation and a thumbs-up from the doc, Serena arrived for this photo shoot barefaced, soft-spoken and still searching for energy. She was wearing a look of concern, as well as basic black joggers and pink-and-white Nike sneakers—all subtle reminders of something that’s easy to forget amid the superhuman facts, figures and fame that are forever fused to her name: she is, ultimately, mortal. That can be easy to forget.
At age 37 and more than two decades into her extraordinary tennis career, Serena became a mega celebrity a long time ago. While finals and forehands were always important, Serena has always, unapologetically, fed her off-court passions, too. Look at what she’s accomplished: GOAT status; four Olympic gold medals; $89 million in prize money and a Forbes-estimated $225 million net worth; a venture-capital firm (Serena Ventures); and a self-funded clothing line, S by Serena.
She’s not the only athlete to cross over into fashion, but she’s arguably done it longer, better and more sincerely than anyone else. “My whole career has been about tennis and fashion,” she says.
In the early 2000s, Serena studied fashion at the Art Institute of Fort Lauderdale. “It wasn’t something that was done—like you can’t focus on two things,” she says. “But I really liked fashion and wanted to learn, and I didn’t want my career to stop. I knew one day I wanted to create this brand that would be for people that have different aspirations and want to be fierce at the same time.”
That’s the same word Serena repeats over and over when describing what she does, both on the court and off. From controversial catsuits and clap back tutus, to personalized collaborations with Off-White designer Virgil Abloh and Nike, and a striking gown-and-sneakers combo as a cochair for the 2019 Met Gala, Serena has served up fashion statements for every occasion. But breaking sharply from the eccentric, distinctive flair of fashion icons and fellow Fashionable 50 stars like Odell Beckham Jr. and Russell Westbrook, Serena’s style is informed by that mortal-ness that was on display in London. Or, as she puts it, “relatable and realistic—with a twist.”
That means putting more spin on a style than she puts on her second serve: feminine tulle skirts paired with chunky combat boots. Or a badass businesswoman blazer one day, then a skin-baring bodysuit the next. It’s curve-hugging, sophisticated silhouettes, but also the universal weekend standard, jeans and a tee. Sometimes her look is sexy in sky-high stilettos. But most of the time it’s comfort in a pair of Nikes.
No matter the look, it’s intended to convey a Serena level of swagger. “I always try to send the message of just being confident and fierce,” she says.
Her direct-to-consumer S by Serena line follows suit: it’s approachable and affordable, but also, according to Serena, up to the quality standards of her good friend the duchess of Sussex, Meghan Markle. The range of basics, loungewear and work-appropriate pieces fits Serena’s vision of clothing that “people can wear every day.”
“Maybe the T-shirt isn’t the most cutting-edge T-shirt, but there’s something about it that speaks to people who aren’t living the Russell Westbrook lifestyle, and she’s very attuned to that,” says Steven Kolb, president and CEO of the Council of Fashion Designers of America, a group of almost 500 American fashion designers. “She understands the power of the message.”
This isn’t her first foray into fashion. In 2004 she launched a brand called Aneres (Serena spelled backwards), and more recently she partnered with Home Shopping Network on a line called Serena Signature Statement; neither took off. She has encountered formidable obstacles since returning to tennis after childbirth and the serious complications that followed, including blood clots that traveled to her lungs and caused a pulmonary embolism. And she’s confronted them all while carrying the weight of yet another new title: working mother. “I’ve faced a lot of criticism,” says Serena. “I think it was kind of preparation for what I’m doing now—[being] a mom.”
While she fell short of her record-tying 24th Grand Slam title at Wimbledon on July 13, she plans to continue competing on a reduced schedule; Serena is also keenly aware of the inevitable expiration date on her storied career. “My dad was like, You can’t just play tennis forever, even though I kind of have,” she says. “For me, it’s important to have something beyond tennis because I have always planned on it.”
That preparation is obvious in the sweeping empire Serena has built off the court. She has big plans for expansion of her fashion line into jewelry and beauty products, while her $10 million investment portfolio (mostly in female and minority-owned companies) is seeing promising returns.
“I just want to take it to the sky,” she says.
Sky, consider yourself on notice.