Anna Kournikova's Complete Transformation Is Gorgeous

Former tennis star Anna Kournikova has long been in the spotlight, but what she's been in the spotlight for has changed. Since 2017, she's seemed to put her focus on raising the three children she shares with singer Enrique Iglesias. Despite the fact that she's been leading a quiet life, Kournikova has had a truly interesting transformation over the years, from being a tennis pro to becoming a model and now settling dow as a mom. Not only that, but she's done charity work and even dabbled in reality TV.

What's even more interesting is that she's had some truly great style moments while juggling all of her ventures. From low-key tenniscore looks to glamorous red-carpet gowns, Kournikova has shown many different sides of herself through her style, all while staying true to her simple and sporty aesthetic. Not only is her laid-back but sultry style enviable (and a great inspiration for anyone interested in tenniscore, one of last fall's biggest trends that is back with a vengeance), but it's also amazing to see the way that she and her fashion choices have changed over the years in ways that are simultaneously dramatic and subtle.

From a young age, Anna Kournikova was all about tennis. A 5-year-old Kournikova was gifted a tennis racket that sparked a lasting interest in the sport, and by age 8, she'd begun playing in junior tournaments. At 14, she was winning major tournaments and was even the youngest player to ever win a Billie Jean King Cup (formerly the Fed Cup) match on behalf of Russia.

Even early on, it's possible to see her sporty and simple style showing through. Often wearing white, Kournikova had an uncomplicated tennis-court style. Wearing tennis shoes and white crew socks along with scrunchies, her accessories were on trend at the time and have a lot of nostalgic charm now. Plus, tenniscore is back in style, so perhaps she's always been ahead of the curve. With her long, blond hair often in a ponytail and her bangs loose, Kournikova looked adorable and at ease on the tennis court.

By 1996, Anna Kournikova's tennis skills were garnering serious attention, and her new coach, Ed Nagel, helped her push herself to reach new heights. She also joined the Russian tennis team at the Olympics in Atlanta that year and competed at the Australian Open, where she was beaten by Martina Hingis.

It wasn't just her skills on the court that were getting noticed, though, as many were also noticing Kournikova's striking style. At an ITF world champions dinner in Paris, Kournikova posed with her award from the previous year and looked completely elegant. With her long, straight hair down and a black spaghetti strap dress on, she looked put-together in a natural, laid-back way. Along with showing off her more glamorous side, her tennis-court style was evolving, too. She started to wear more form-fitting looks and strayed away from simple white outfits by including more colors (like black and red), all proof that she didn't need a guide to styling a chic tennis skirt.

By 1998, Anna Kournikova's name was becoming well-known in the tennis world. In 1999, Kournikova won a grand slam doubles title with partner (and former rival) Martina Hingis. The dynamic (and stylish) duo even began calling themselves "the Spice Girls of tennis." While Kournikova hit some career milestones playing with Hingis, their partnership didn't last long and was rumored to have a rocky ending.

On the court, Kournikova often wore tennis dresses and skort and tank outfits, as well as shorts and athletic tees. However, it was her style off the court that was really catching attention. At the Express Find the Next Model Search Finals, she wore a bold red dress and her long hair in voluminous curls. Not only did she look sophisticated, but this super glam style was also a complete 180 from her athletic wear looks.

By Y2K, Anna Kournikova's tennis career was just heating up. She broke into the top 10 at the Australian Open and ranked number 8 in the world. She also landed big endorsement deals, like the one she had with Berlei as the face of its shock absorber sports bras. She also dabbled in acting, with a small role in the movie "Me, Myself & Irene." She also had the distinction of being the most Googled woman of the year.

Her style was blooming, too. On the court, she often wore matching tank and short sets, and fitted tennis dresses in simple colors like black, white, and navy blue, with her hair frequently in a tightly braided ponytail. Off the court, her style was low-key but trendy with a sultry edge. At a children's charity tennis match, she donned a super-stylish denim halter dress. When her ad campaign with Omega watches was unveiled at an ESPN Zone event she wore black pants with a sheer black and red patterned blouse that tied in the front. Both of these looks highlight her penchant for simple styles with a lot of impact.

In 2001, Anna Kournikova's tennis career was on hold, as multiple injuries made competing difficult. While she dropped out of Wimbledon and the Australian Open, she pushed her career in front of the camera further and met her future partner in the process. That year, she appeared in Enrique Iglesias' music video for his song "Escape." Not long after, they made their relationship public. By 2002, they walked their first red carpet together at the MTV VMAs. Not only was this the world's introduction to them as a couple, but it was also an insight into Kournikova's developing style.

The all-white outfit she wore to the VMAs that year was truly iconic. She elevated her low-rise white jeans by pairing them with a cut-off tank that highlighted her figure and popped with her tan. White became a signature color for her around this time, both on and off the court. Her makeup and hair were simple, with her tresses lightly tousled in gentle, beachy waves and her makeup minimal.

At 21, Anna Kournikova officially put tennis behind her, as multiple injuries made it too difficult for her to continue competing. In a 2011 interview with People, Kournikova looked back at her early retirement, saying, "I never planned or thought that was going to be it. My back really forced me to stop. It got so bad; I couldn't tie my shoes, literally. I would be in excruciating pain." She also opened up about the path she had to take to rediscover who she was without tennis: "I did everything from therapy to 10-hour walks on the beach to discover, and think, and try new things."

While Kournikova might have felt adrift without tennis, she seemed to grow more comfortable in the spotlight. White was still a go-to color for her when she attended the afterparty for "Once Upon a Time in Mexico" in an asymmetrical skirt and cropped top. She accessorized with a silver belt, a long, silver cross necklace, and strappy silver sandals. However, at the Monte Carlo Music Awards, she seemed to be branching out, at least in terms of color. Her sheer green dress and hot pink lipstick created an eye-catching contrast.

On her path to rediscover herself, Anna Kournikova tried lots of different things. Not only did she model and grace magazine covers, like Sports Illustrated, but she also dedicated herself to charity work. Writing for Oprah.com, Kournikova opened up about the emotional impact of her work in Russia with Humanitarian Action had on her. She detailed spending time with a young mother she met, writing, "I imagine their lives. Her, a single mother living on the streets, no family, no home, no food, nothing...and those two beautiful girls being raised in such a difficult situation. It's hard for me to walk back in, but I do."

During this period, Kournikova made appearances at fashion shows, promotional events for her Simplicity fragrance, and awards shows, including the Teen Choice Awards. Little black dresses with minimal accessories became a go-to look for her, proving she knew the best casual ways to style her favorite LBD. For more laid-back looks, she often wore low-rise flare jeans with polo tees or baby-doll tops. Talking to Sports Illustrated, she opened up about all of the media attention she and her boyfriend, Enrique Iglesias, were receiving, saying, "Girls look at him. Guys look at me. It goes with the job, but it gets annoying when you feel violated. Just take the picture and be done." We can't blame her there!

At the start of the 2010s, Anna Kournikova was still modeling, appearing on the cover of Maxim for the fourth time. That wasn't the only big thing that happened to her that year, though, as she also officially became a United States citizen. In her interview with Maxim, she discussed what her citizenship meant to her, saying, "I've always considered myself half-Russian and half-American. It never seemed to really matter if I had a passport or not. But when I started working with the [United Services Organizations] and the troops overseas, it just seemed the logical next step" (via Tennis.com).

Kournikova's style was also entering a new phase around this time, with some of her all-white tennis looks reappearing as she competed at Wimbledon in Legends doubles with her old partner, Martina Hingis. She also had a new go-to going-out look, which was a black blazer, black dress shorts, and a classic going-out top. Basically, you can retire certain clothes or from a sport, but they always come back in some capacity. 

By 2011, Anna Kournikova was taking her career in another direction, replacing Jillian Michaels as a trainer on "The Biggest Loser." Kournikova got attention for trying to bring something new to the show, but the stint was short-lived, as she ultimately didn't feel it was the best "fit for her," as a source told People at the time.

She seemed as comfortable as ever in the spotlight, though, and looked amazing in the jeans-and-jacket outfits she wore to promote the show. When she wasn't working as a trainer, she was often snapped in pics with her long-time boyfriend, wearing comfortable but cool-looking outfits featuring black cut-off shorts, long-sleeved open sweaters tied in the front, and black combat boots. At the BAFTA Brits to Watch event, she dialed up the glamour by wearing one of her most dramatic looks yet. She seemed to be going outside her comfort zone, and the teal dress she wore with gold platform heels was much more structured than her typical looks.

By 2012, there was a lot of speculation about Anna Kournikova's personal life. She and Enrique Iglesias had been together for about a decade, and many were curious about their relationship status and future plans. Talking to Women's Health the previous year, Kournikova said of relationships, "[Marriage] isn't important to me. I'm in a happy relationship — that's all that matters," before adding, "I believe in commitment. I believe in being open and trusting each other and respecting each other completely."

While she didn't seem too interested in marriage, having children was another matter. In the same interview, she said, "I absolutely want to have children, whether I have my own or adopt. I love taking care of people." True to those words, around this time, her focus seemed to shift from her career to being a supportive partner, as she was frequently seen attending parties with Iglesias and dancing at his concerts. That year, her style was defined by her trademark simplicity and favorite colors, black and white. She was often seen in tanks and jeans, and she frequently wore her hair in a high ponytail. Altogether, her style exuded a down-to-earth femininity that had a lot of understated appeal.

In 2013, Anna Kournikova seemed to have taken a step back from public life, but that didn't mean she took a step back from posting on Instagram. While she may have been keeping to herself in many ways, she still showed off her style. Along with some selfies and adorable pics of her dog, she posted photos of herself hanging out at the beach, working out, and traveling. Another mainstay of her grid from this era was her going-out looks.

In a post from 2015, we get a look at a type of outfit that reappears over the years. Paired with some black cut-off shorts, Kournikova wore a white T-shirt with a dark gray button-down layered over it. Accessorized with edgy black booties and a stack of bracelets on one arm, this look has a lot of subtle edge. In another going-out style from early 2016, we get another look at how she reworks similar elements to make fresh looks. This time, she wore black skinny pants with black booties, a chic black blazer, and a white and black polka-dot button-up shirt underneath. She paired the look with layered bracelets and a simple black bag, which resulted in an outfit that looked both comfortable and polished.

Anna Kournikova's Instagram posts from 2017 are all about one thing: the beach. Whether on a boat, swimming, or hanging out with her dogs, Kournikova posted lots of photos by the water and rocking swimsuits, too. Just as with the rest of her wardrobe, basic colors like black and white make up a lot of her swimsuit styles, from white string bikinis to white cover-ups paired with black sun hats. Not only that, but there were lots of times Kournikova went make-up-free and looked flawless. Oh, and we can't forget her rocking chic, dark sunglasses, either.

One of the biggest things that happened for Kournikova that year, though, was kept completely under wraps. At the end of 2017, she and her long-time love, Enrique Iglesias, welcomed a pair of twins named Nicholas and Lucy into the world. It seemed that now, several years after expressing the importance of becoming a mom to her, Kournikova finally got to start her own family.

While family life seemed to be Anna Kournikova's primary focus between 2018 and 2020, she still made time for other things, including modeling. In 2019, she did a photoshoot for Cosmopolitan Russia (now called The Voice Mag and no longer affiliated with Cosmopolitan), proving that she was an expert at rocking a bikini on a magazine cover — and as stylishly as ever.

Notoriously private, Kournikova kept a lot of her business firmly to herself. That said, she gave glimpses of her life as a mom on her Instagram. From cute videos of her rocking adorable space buns and dancing with her baby to workout pictures and throwback pics of herself in an all-black outfit holding her growing baby bump, Kournikova shared what her life as a new mom was like on her terms.

In 2020, Kournikova had even more to share, as she gave birth to her third child. While having a baby at the start of the COVID-19 pandemic might have been difficult, Kournikova seemed overjoyed, glowing in the photos of her giving birth that she shared on Instagram about a month later.

In the early 2020s, Anna Kournikova still protected her privacy, but she gave little peeks into her domestic life from time to time. Her hands were undoubtedly full with her three young children and two dogs, but it seems that after her busy tennis career and her time soaking up the spotlight, she's more than happy to spend her time with her family.

Even though there aren't too many snapshots of her style from this time, it seems pretty likely she's sticking with a lot of her style standbys. In a post wishing Enrique Iglesias a happy birthday, she included a photo of herself with him and their three children. She can be seen in an all-black outfit that she accessorized with a pearl necklace, a cross necklace, and a light pink bow in her high ponytail. Except for the bow, all of these elements are ones that she's been rocking for years and that still bring a subtle edge to her look while also being super put-together.

By 2024, Anna Kournikova is as low-key as she's ever been. In fact, she rarely makes appearances anymoe, including on her own Instagram page. Instead, she shares pics of her children and partner. It seems that now more than ever, she's putting a lot of energy into being a supportive partner and mom. 

During a conversation with SiriusXM's "FYI Show," Enrique Iglesias got candid about his life as a performer and how Kournikova takes it in stride, saying, "Anna will be at one of my shows and I'll do that. ... I love embracing, kissing and hugging my fans." The "I Like It" singer added, "And a lot of times she [says], 'Man, I always get this look from some of the girls ... and they'll ask, 'Are you OK with it?' Yeah, I'm totally cool. He's onstage. He's embracing his fans'."