The Stunning Style Transformation Of Serena Williams

When it comes to women in tennis, one name that immediately comes to mind is Serena Williams. The talented athlete has shown brilliance on the court for almost three decades, and while her legacy in tennis is undeniable, today, our focus is Williams' fashion game. Yes, she may be one of the most famous athletes in the world, but what many may not know is that Williams is also incredibly passionate about fashion. "I like to say I went to fashion school in between winning Wimbledons," she told Teen Vogue in 2020 — and she wasn't joking.

While some celebs just enjoy fashion, Williams has truly used it as a way to express herself, whether on court or at industry events. Looking back on her fashion choices as a teen and in the early 2000s, her fashion transformation — and the power it holds — is undeniable. Williams has shown fans across the globe how to be themselves, and that legacy is far more important than her tennis wins. Of course, at Glam, we adore fashion, so we may be a bit subjective.

When Serena Williams was a teen kicking off her professional tennis career, it was clear that she was not only immensely talented but that she also had the need to express herself through her style — and use that as a means to showcase just who she is. "I knew when I was a little girl that I was different, so I explored fashion and style as a way to kind of distinguish myself," the athlete said in 2023 while accepting the Fashion Icon award at the CFDA. "I loved reimagining the traditional tennis outfits so I designed skirts out of denim and I wore purple tutus and bodysuits and knee-high boots and put beads in my hair, and braids. It was really just a fun time for me."

While fashion was still in the backseat for her (at least as far as the public perception goes), the truth is that Williams always loved clothes — something her mother helped her nourish. "My mom taught me how to sew when I was super young; I used to make clothes for my dolls," Williams told Glamour in 2016. "When I finally went to [fashion design] school [in 1999], I really took to pattern making. Everyone in class was good at something; I was the person, if you need help with your patterns, you come to me and I would help you out." And while she hadn't kicked off her career in fashion just yet, teen Serena Williams was using every tennis match to make sure her look was memorable.

By the early 2000s, the Williams sisters were global superstars known for their incredible tennis performances — and with that kind of fame, they found themselves walking all types of red carpets. Often together, the two would usually coordinate their looks, serving us Y2K fashion similar to what Paris Hilton rocked in the 2000s.

In 2000, Serena and Venus Williams attended the Teen Choice Awards, where they were awarded the first-ever Teen Choice Award for Extraordinary Achievement. For the occasion, the sisters opted to go for matching pink looks that clearly showcased how the two were a team, yet still individual and unique. While Venus wore a pink strapless corset covered in sequins and low-rise pink pants, Serena decided to go for a strapless minidress. Both looked incredible, and this look undoubtedly foreshadowed just how passionate they were about fashion.

As we were approaching the mid-2000s, Serena Williams' style began showing more and more. One of her most memorable fashion moments of the era happened in 2003, when she walked the ESPY Awards red carpet in an eye-catching pink dress — and one that she actually designed herself. The outfit featured a deep-V neckline and a high slit, resulting in a very sultry look. 

At the time, the tennis player was in her early 20s, but fashion was already shaping up to be a big part of her career. In an interview with Oprah Winfrey in 2003, Serena's sister Venus Williams revealed the two shared their passion for anything fashion-related. "Serena and I went to fashion design school, so we're not just walking around saying, 'We want to be fashion girls,'" Venus said (via Oprah). "We're actually educated in the matter." In 2004, Serena launched her clothing line "Aneres." 

Regardless of whether she was showcasing her style on the tennis court or at a fancy industry event — one thing quickly became clear: Serena Williams loves bold and fun colors. From playing the game in a hot-pink tennis dress to walking down a red carpet in a blue maxi dress — there truly wasn't a color Williams couldn't pull off. In fact, her game-day style was so unique that it was often covered by news outlets alongside her athletic performance. For Williams, it was a no-brainer that tennis and fashion go hand in hand.

During this period, the professional athlete also began embracing her natural hair texture more frequently, allowing her curls to shine. However, Williams also loved exploring different hairstyles, all of which always served as an accessory to her fashion choices.

As the end of the 2000s was approaching, regardless of whether you followed tennis or not, you probably knew Serena Williams was a fashionista. "Fashion has always been a main part of my tennis game," the star told Vogue in 2009. "When you look good, you really take pride in what you do. And for me, that means I play better." In 2009, she wore a stunning light-teal Roberto Cavalli gown to the ESPY Awards, once again establishing herself as an athlete who knows a lot about style.

Of course, fashion is often subjective, and Williams has made it a point to wear what she likes, regardless of whether it is cool or not. Naturally, this also resulted in some critique of her style over the years, but the tennis player doesn't take it personally. "I've been on the worst-dressed list several times, and I don't care," Williams told People in 2009. "I like what I like, and if I feel good wearing something, I'll wear it." When asked what fashion piece makes her feel good, Williams replied, "A belt. I love belts. All my fashions tend to have belts. I'm obsessed with them. You can put a belt on any outfit and make it perfect." While the belt look has defined that time period, in 2024, statement belts are trending again.

As the early 2010s kicked off, Serena Williams was a staple at not only sports events, but also any entertainment events that involved looking fabulous. One event the star rarely missed was the Vanity Fair Oscar Party. In 2011, she attended the star-studded bash in a coral strapless Ines Di Santo dress, and a year later, she attended the party in a backless yellow mermaid gown by Christiane King. "If it involves sitting down or shopping, I'm excellent at it," Williams joked in 2012 (via Daily Mail). But while the tennis star certainly enjoyed exploring fashion, she also loved creating it.

In a candid conversation with Time in 2012, Williams opened up about her brands. "I have two. There's Serena's Signature Statement ... And I have Aneres, which is my name spelled backwards," the star gushed. "I love designing dresses and tops. I went to fashion school, and I'm starting to have to do bags and stuff, and I didn't do bags in school because my whole thing was dresses. I even did menswear. Bags have been super challenging for me. But it's fun. I'm also starting a jewelry line. It's going to be part of Aneres." While she was still one of the best tennis players in the world, Williams' dream of transitioning into the fashion industry was more and more evident with every fashion project she started.

As Serena Williams was in her early 30s, it was clear that her personal style was evolving, allowing her to experiment with her look in various ways. "I think my style has definitely evolved," she admitted in 2013 (via The Advertiser). "I love to push a trend on court but in my own closet, I don't push it a lot. I'm not as daring as I am in public. I prefer classic styles and I love to mix them with a little trend," the tennis star added.

In 2014, Williams attended the Vanity Fair Oscar Party in a stunning yet daring Michael Costello gown that featured sheer cutouts in multiple spots. The look was elegant yet sultry, proving that Williams knows how to balance her fashion to hit that sweet spot perfectly.

Throughout the mid-2010s, Serena Williams was taking her work in fashion more seriously, and in 2015, she even had her first New York Fashion Week show. "Throughout my life, I've always believed in pushing boundaries ... whether it's in tennis, business, or fashion," Williams wrote in a statement before the show (via Daily Mail). "By offering my Signature Statement collection exclusively through an innovative retailer like HSN, I'm able to communicate directly with my fans," she added.

During the time, Williams herself was embracing edgier looks, often wearing intricate black dresses to industry events. Cutouts and lace seemed to be the star's favorite, as they provided an easy way to spice fashion up."I love fashion a lot. I went to school for fashion. I was somehow playing professional tennis and going to college," the tennis player said in 2016 (via Footwear News). "That's my release, and I'm doing a lot more of that now. I need other stuff to keep me sane."

In 2018, Serena Williams launched her Serena collection, marking her path in the fashion industry even more. "This is my life. The athletic wear is what I do, my everyday life. I love the biker shorts," she told W in 2018. In September 2017, the tennis player and her husband Alexis Ohanian welcomed their first child, and Williams admitted that being a mother changed how she looks at fashion."I definitely found that my style changed with the baby," Williams said in the interview. "I'm still nursing, so I always need something with easy access or just something that the baby can spit up on or throw food at me in. My style has definitely evolved, but that doesn't mean that I can't look good."

In 2019, Serena Williams attended the Met Gala, also known as the fashion event of the year, and for the occasion, she wore a yellow Versace gown covered in 3D pink leaves which she paired with yellow Nike sneakers. In an interview with Vogue in which she was reflecting on her biggest fashion moments, Williams actually revealed that it was Anna Wintour who suggested she wear sneakers. "I was co-hosting the Met Ball this year," Williams reflected in a feature for Vogue. "We thought of this literally the night before, and so we had to get these shoes to me. When I was on the red carpet, I wanted everyone to see that I was actually wearing these really cool Virgil Nike shoes that actually really matched perfectly to the dress," she added. The look definitely became one of the most unforgettable of the night — and Williams remained true to herself and her style, which is incredibly important for a prestigious fashion event like the Met.

As we entered the 2020s, it was clear that Serena Williams was a fashion icon who played in her own league. From her casual outfits to her red-carpet moments, the athlete wasted no time on looks that weren't incredible. "It's so fun to have fun with fashion and in my sport, I have a great opportunity to play in something really wide and really fun, and to really express myself because sometimes those people, they only see me on the court," she told Teen Vogue in 2020, adding that people don't realize that she has also been in the fashion industry since the 2000s.

In 2021, Williams attended the Met Gala in a Gucci bodysuit with an ombré-pink faux-fur cape on top. "This is so major, this is Gucci, hello," the tennis star gushed about the look to Vogue in 2023. "I said, 'My outfit is amazing that you designed, but it's not Serena ....' So they created this in like a week, and I was like, 'What if I just wear a bodysuit? Like, just give me something different." Together, the brand and the athlete definitely created a look that was eye-catching and different from the gowns we're used to seeing on the event's red carpet.

2023 marked a major year for Serena Williams — not just because she and her husband welcomed their second daughter. In 2023, the athlete was honored by the Council of Fashion Designers of America with the Fashion Icon award. "In many ways for me, the tennis courts became my runway, and the U.S. Open was my own New York Fashion Week," she said in her acceptance speech (via CFDA). For the occasion, the star donned a dramatic black Thom Browne gown covered in sequins.

In a candid conversation with Marie Claire in 2024, the tennis player — who retired from the game in 2022 — reflected on her impact on fashion in sports. "[S]eeing myself and my sister on the big stages of Wimbledon and the U.S. Open, being ourselves and wearing great outfits and looking our best, really changed women's sports — which is crazy," Williams said. "Now you look at all these amazing women athletes, whether they're in basketball or another sport, they want to be glamorous on the court now, too."

That same year, Williams also talked to People about fashion mistakes. "Listen, I think being on worst-dressed lists is important," the star told the outlet. "I've had a lot of outfits. A lot of on-court outfits, a lot of off-court outfits. I've had some amazing, amazing red-carpet looks. I've had a lot of different looks, but you know what, you can't take any of it back. I'm leaning into all of them." For her 2024 Met Gala look, Williams went with a stunning golden Balenciaga gown that not many could have pulled off. However, with her strong personality and a keen eye for detail, Williams was definitely a winner — and she didn't make it onto the 2024 Met Gala's worst-dressed list.

Today, Serena Williams is known just as much for her style as she is for the sport that made her famous. Whether she's attending the Vanity Fair Oscar Party in a breathtaking black Dolce & Gabbana gown that is giving legs for days or dancing in a blue skirt and button-up set on stage during the Super Bowl halftime show (expertly avoiding making our worst-dressed celebs at the 2025 Super Bowl list) — Williams may have retired, but her career hasn't stopped.

Now in her early 40s, we have no doubt that Williams will continue using her fame and her platform to share her passions and showcase what being authentic truly means. And as far as her fashion evolution goes, we're thrilled to see just what the future holds for the most famous tennis star to date! Now, if you are a fan of women in tennis, check out Anna Kournikova's lavish life next!