Serena Williams went pro in 1995 when she was just 14 years old, jumpstarting her journey as a tennis icon. It wasn’t long after that she became a style star either, showing up to matches wearing bold and innovative looks.

Over the course of her 27-year career, the athlete’s tennis outfits often reflected her personal style, including many bright colors, patterns and unexpected silhouettes. The 23-time Grand Slam champ has taken to the court in everything from catsuits and color-block dresses to statement jewelry and coordinated sneakers, pushing the boundaries of what is acceptable in the world of tennis (which has not been without controversy).

When the tennis legend retired after the 2022 US Open, she went out with a style bang. For one of her matches, she wore a Nike figure skater-inspired look decked in crystals. She paired the dress with custom diamond-encrusted NikeCourt Flare 2 sneakers emblazoned with a golden “SW” on the side.

Her older daughter, Olympia, has also been known to twin with the athlete, and has even paid homage to some of Serena’s most memorable tennis looks!

Here’s a look back at some of Serena Williams’ best fashion moments on the court.

Serena Williams playing tennis in 1992

Long before she went pro and earned major sportswear sponsorships, Williams was putting a fashionable spin on the traditional tennis outfit. She wore this white-and-blue two-piece ensemble with a floral design during a match in 1992 — clearly the start of her penchant for flouncy skirts and bold patterns.

Serena Williams at the US Open in 1999

Williams won her first US Open at 17 years old in 1999, wearing a bright yellow Puma dress with black-and-white accents. She paired the simple and chic ensemble with gold hoops and white and topped the look off with white and yellow beads in her hair. Williams and her older sister, Venus Williams, were known to sport these hair accessories often early in their careers.

Serena Williams at the US Open in 2000

Taking the tie-dye look for a spin, the athlete experimented with patterns at the 2000 US Open. She chose a black-and-purple tie-dye dress by Puma for day two of the competition, later wearing a color-block reiteration of the dress in the quarterfinal round.

Serena Williams at the US Open in 2001

This was a master class in coordination: Williams donned a yellow Puma dress with black accents for her semifinals match at the 2001 US Open. She complemented the two-tone look by pairing it with matching Puma sneakers and silver jewelry.

Serena Williams at the Eurocard German Open in 2002

Going for a brighter and glitzier style, the athlete sported a metallic coral dress by Puma for the 2002 Eurocard German Open. Never afraid of a statement piece of jewelry, Williams accessorized this outfit with a heart pendant and gold watch.

Serena Williams at the US Open in 2002

While Williams often wears tennis dresses on the court, she left behind her signature look at the 2002 US Open — opting for a fashionable catsuit instead. Winning her second singles title at the event, the athlete walked onto the court in a black sleeveless unitard by Puma, as well as pink-and-white sneakers.

Serena Williams at the Australian Open in 2003

Williams competed at the 2003 Australian Open in an orange-and-white Puma dress with a rhinestone-encrusted strap. She wore variations of this outfit throughout the competition, pairing this ensemble with matching sneakers and her go-to heart pendant.

Serena Williams at the NASDAQ 100 Open in 2004

Leave it to Williams to bring a corset to the court! The tennis player showed up to the 2004 NASDAQ 100 Open in her first custom outfit by Nike (she signed a contract with the brand in late 2003). The ensemble was a bold choice, as the athlete paired a white dress with a metallic corset belt and a white headband with “Serena” bedazzled across the top.

She opened up to ESPN about the look at the time, saying, “I said [to Nike], ‘Look, I’m really into looking really good on the court. I don’t have to be very comfortable.’ If you guys want to change it up and use different fabrics that a lot of players don’t want to wear because they’re really into comfort and really into being able to perform, I am, too, definitely, but I don’t have to be as comfortable as the next player.”

Serena Williams at the French Open in 2004

In a grand return to her vibrant ensembles, Williams opted for an all-pink outfit on day two of the 2004 French Open. The hot pink attire consisted of a zip-up top and flowing skirt with a red waistband. She completed the look with matching sneakers, a headband and large hoop earrings.

Serena Williams at the US Open in 2004

Embracing early aughts fashion, Williams made a case for denim on the tennis court during the 2004 US Open. She took her court style in an edgier direction with this statement look featuring a studded black Nike tank top, black sneakers and a pleated denim mini skirt.

Serena Williams at the US Open in 2004

Williams continued on her edgy streak with a biker-inspired look during the third round of the women’s singles at the 2004 US Open. She played her match wearing a studded black Nike dress with a pleated skirt and matching gladiator-style boots. The athlete was also spotted warming up in a studded leather jacket to round out the striking ensemble.

Serena Williams at the Australian Open in 2005

The tennis player rocked her own design from her first collaboration with Nike — The Serena Williams Collection — at the 2005 Australian Open. She won her first title at the event in this neon-green-and-white convertible dress, completing the look with another pair of knee-high Nike boots.

Serena Williams at the NASDAQ 100 Open in 2005

Williams showed up at the 2005 NASDAQ 100 Open in another catsuit, this time in a hot pink hue. The zip-up unitard featured white accents, a keyhole back and netted side panels. She, of course, topped off the ensemble with matching sneakers, a headband and heart drop earrings.

Serena Williams at the US Open in 2006

Taking a short break from bright colors, Williams started incorporating subtle patterns into her style with this navy Nike dress that included red, orange and gold designs. She kept her accessories simple this time, sporting gold hoop earrings and a matching chain necklace.

Serena Williams at the Australian Open in 2007

Back with a bang, Williams returned to colorful outfits in this neon-green-and-yellow Nike dress for the 2007 Australian Open to collect her first win at the event in two years. In one of her more casually chic ensembles, the athlete also wore white sneakers and multi-colored hoop earrings.

Serena Williams at Wimbledon in 2008

Even with an all-white dress code — a requirement at Wimbledon — Williams always found a way to make a look her own. The tennis player showed up on the court donning a sleek white trench coat over her dress as only a fashion icon can. She doubled down on her trendsetting look, appearing at Wimbledon the following year in another trench coat ensemble.

Serena Williams at the US Open in 2008

In an outfit made for a comeback win, Williams donned a bright red ensemble for the 2008 US Open, where she took home the title — beating her sister Venus in the quarterfinal. The simple outfit included a Nike dress with a pleated skirt, a headband and red-and-white sneakers.

Serena Williams at the Australian Open in 2010

Trading bright red for neon orange, Williams wore this vibrant dress to the 2010 Australian Open. The athlete successfully defended her reigning title, winning the competition despite her injuries. (She wore leg wrappings on her thigh and knee).

Serena Williams at the French Open in 2010

A lover of pleated skirts, Williams sported a dress with a ruffled trim in an especially vibrant teal hue for the 2010 Australian Open. Complete with neon green undershorts, a matching headband and white sneakers, this ensemble was one of the athlete’s more classic tennis outfits.

Serena Williams at the French Open in 2012

Two years later, Williams walked onto the court at the French Open in another head-to-toe teal ensemble. While she didn’t take home the title this year, she still stunned in this Nike look — consisting of a gradient dress and teal-and-white sneakers, as well as a matching headband and wrist sweatbands.

Serena Williams at the US Open in 2012

Taking home the trophy at the US Open for the first time in four years calls for two eye-catching numbers. For her daytime matches, Williams wore this pink-and-navy-blue pleated dress with neon green undershorts and navy blue sneakers. She later changed into the same color-block dress in navy-blue-and-neon-green for her winning match.

Serena Williams at the WTA Championships in 2012

Williams took a patriotic approach to her Nike ensemble for her WTA Championship match against longtime rival Maria Sharapova in Instanbul. The red, white and blue ensemble — featuring a collared tank top, pleated skirt and matching sneakers — must’ve been her good luck charm, as she came out on top in the final.

Serena Williams at the Australian Open in 2013

Bringing two of her go-to style choices together, the athlete coordinated bright colors and bold patterns for her 2013 Australian Open ensemble. The orange, purple and black color-block Nike dress was the centerpiece of her bold look. She paired the vibrant dress with neon orange sneakers and a matching headband, which both included a black pattern.

Serena Williams at the US Open in 2013

Continuing her streak of color-block dresses, Williams opted for a red-and-peach Nike dress at the 2013 US Open. Taking home the title for the second year in a row, the player added even more color to her look with navy blue undershorts, a matching headband and neon-red-and-navy-blue sneakers.

Serena Williams at the Sony Open in 2014

The athlete made a splash in this aqua-and-orange Nike dress at the 2014 Sony Open, which was surely a nod to the city where she lives — Miami — and their football team. (Williams and her sister are minority owners of the Miami Dolphins organization). She fully committed to the look, accessorizing it with a neon orange headband, wrist sweatbands and sneakers.

Serena Williams at Wimbledon in 2014

Shaking up Wimbledon fashion yet again, the player suited up for the competition — literally. Williams walked on the court in the required all-white ensemble, wearing a sleek Nike blazer over a dress with a striped pattern on the skirt. She finished off the unconventional look with black-and-white accessories and silver jewelry.

Serena Williams at the US Open in 2014

For her third consecutive US Open win, Williams wore an outfit that really popped against the backdrop of the green tennis court. The athlete donned a hot pink leopard-print dress by Nike, completing the striking look with a matching wrist sweatband, a pink headband and white-and-pink sneakers.

Serena Williams at the Australian Open in 2015

Taking the vibrancy up a few notches, Williams’ outfit at the 2015 Australian Open was a mix of neon colors. Combining a hot pink two-piece ensemble with a neon yellow cut-out dress, the athlete was ready to make a statement with her fashion and her tennis — winning her 19th major singles title in the final round against Sharapova.

Serena Williams at the French Open in 2015

Signaling the start of several patterned looks, Williams dominated the 2015 French Open in a two-tone orange number. The leopard-print skirt elevated the simple silhouette of this Nike dress, which she paired with matching sneakers and a magenta headband.

Serena Williams at Wimbledon in 2015

Williams pushed the limits of Wimbledon’s dress code with her leopard-print outfit at the 2015 competition. The sheer skirt on the ensemble was a bold choice that showed the athlete wasn’t afraid to take a few fashion risks. Instead of accessorizing with her usual statement jewelry, she kept it minimal with dainty silver jewelry.

Serena Williams at the US Open in 2015

The athlete competed at the 2015 US Open wearing a series of snakeskin-print dresses, but this black-and-red one she wore for the third round was especially noteworthy. A departure from her favored vibrant hues, this Nike ensemble featured a keyhole back and matching sneakers.

Serena Williams at the Australian Open in 2016

It doesn’t get more vibrant than canary yellow, and Williams rocked a crop top and pleated skirt in the bold hue for her match against Sharapova at the 2016 Australian Open. The athlete expressed that the look was a result of her desire to bring pop culture to the tennis court.

“It was definitely my design, something I actually sketched, you know. So I just wanted to think outside of the box,” she said, according to the Herald Sun. “I’ve been on tour for a long time. I’ve been wearing so many different designs. I just wanted to push the envelope again, just bring pop culture to tennis, kind of make it really fun. A lot of things you see on stage and, you know, just in that pop culture world, I wanted to bring that youth and that fun-ness to it.”

Serena Williams at the French Open in 2016

Williams makes you think cut-outs were made for the court with this blue Nike dress she wore over black leggings for the 2016 French Open. As daring as the side cut-outs are, perhaps the most eye-catching detail of this ensemble is the rose pattern that covers the Nike symbol on her sneakers.

Serena Williams at the US Open in 2016

For her first match of the 2016 US Open, against Ekaterina Makarova, Williams took it back to a traditional tennis style with a black-and-pink pleated Nike dress, black sleeves and coordinating sneakers. The tennis star told Vogue at the time that she “wanted to bring classic back to tennis” by putting a modern spin on the customary look using one of her favorite colors — pink.

Serena Williams at the Australian Open in 2017

Williams won her 23rd Grand Slam singles title at the 2017 Australian Open wearing a black-and-white graphic dress by Nike. While her victory was historic, the win was made all the more impressive when the athlete later revealed she had played in the tournament while pregnant with her first child.

Serena Williams at the French Open Tennis Tournament in 2018

Almost a year after giving birth to her daughter, Williams returned to the court in a black catsuit for the 2018 French Open. The striking look sparked controversy, with the French Tennis Federation President Bernard Giudicelli banning the catsuit from future matches.

“I feel like a warrior in it,” Williams told reporters of her ensemble at the time. “I’ve always wanted to be a superhero, and it’s kind of my way of being a superhero.”

“I’ve had a lot of problems with my blood clots, God I don’t know how many I’ve had in the past 12 months,” she added. “I’ve been wearing pants in general a lot when I play so I can keep the blood circulation going.”

Serena Williams at the US Open in 2018

Bringing ballerina attire to the court, Williams rocked a purple-and-brown tutu dress at the 2018 US Open. The fashion-forward look was a collaboration between Nike and Virgil Abloh of Off-White. In an interview with Vogue editor-in-chief Anna Wintour, Williams said this one-sleeve ensemble was one of her favorite tennis looks of all time, and she still wears it off the court.

“I think it’s so fun to have fun with fashion and in my sport, I have a great opportunity to play in something really wild and really fun and really express myself. Most people only see me on the court,” she said.

Serena Williams at the Australian Open in 2019

A little controversy didn’t stop the athlete from bringing adventurous fashion to a match. After the ban of her catsuit at the French Open in 2018, Williams showed up to the 2019 Australian Open wearing a bright green romper. In a bold move, the player paired the sleeveless Nike jumpsuit with black fishnet stockings.

Serena Williams at Wimbledon in 2019

Williams sported another daring ensemble at Wimbledon in 2019, kicking off her first match in a white Nike dress with midriff cut-outs. The athlete is known for her fashionable takes on the competition’s limited dress code and accessorized this look with matching sneakers, a watch and hoop earrings.

Serena Williams at the Australian Open in 2020

In a head-to-toe purple outfit, the tennis player brought back her signature free-flowing dress silhouette with this leopard-print Nike number. While she coordinated her accessories — sneakers and a headband — with her ensemble, the finishing touch was her koala manicure, a nod to her host country.

Serena Williams at the US Open in 2020

A rare fashion moment, Williams opted for a neutral color scheme at the fourth round match of the 2020 US Open. However, she couldn’t resist adding a small pop of color to the beige outfit with a set of red wrist sweatbands.

Serena Williams at the French Open in 2021

Swapping neutral for neon, the athlete’s outfit for the 2021 French Open was highlighter green from top to bottom. The Nike dress had a subtle black pattern and an asymmetrical strap for an eye-catching look that wasn’t too over-the-top. Look closely and you’ll see the personalized inscriptions on her sneakers reading “Serena Willy” and “queen.”

Serena Williams at the WTA 500 Yarra Valley Classic in 2021

A classic look with a modern twist, Williams brought back the pleated skirt for her quarterfinals match against Danielle Collins at the 2021 WTA Yarra Valley Classic. The hot pink Nike ensemble included a tank top, a pleated skirt with a black waistband, matching sneakers and silver jewelry.

Serena Williams at the Australian Open in 2021

Williams made waves once again with her asymmetric, color-blocked, one-legged catsuit at the 2021 Australian Open. The pink, red and black Nike ensemble was worn as a tribute to track star Florence Griffith Warner who famously ran in one-legged catsuits.

“I was inspired by Flo-Jo, who was a wonderful track athlete, amazing athlete when I was growing up,” the player said after the match, according to ESPN. “Watching her fashion, just always changing, her outfits were always amazing.”

“This year we thought of what can we do to keep elevating the Serena Williams on the court. The Nike team actually thought of this design of inspiration from Flo-Jo. I was like, ‘Oh, my god, this is so brilliant,’ ” she added.

The player completed her striking look with a blue headband, blue-and-pink sneakers and a “queen” necklace from her own jewelry line.

Serena Williams at the Internazionali BNL D’Italia in 2021

The tennis legend wore a pastel pink outfit during a match in Rome. Social distancing laws prohibited fans from entering the venue, but the athlete still created a noteworthy look featuring a short-sleeve shirt that was knotted in the front, a pleated skirt with a black waistband and matching accessories.

Serena Williams at the US Open in 2022

Williams pulled out all the stops for the last tennis competition of her illustrious career. She took to the court at the 2022 US Open in a figure skater-inspired look by Nike that included a crystal-embellished dress with sheer sleeves and diamond-encrusted NikeCourt Flare 2 sneakers with “SW” embossed on the side in gold.

An outfit fit for a tennis legend, she accessorized the dazzling look with Swarovski crystals in her hair, a crystal-studded hairband and silver jewelry.