Anna Kournikova's Fashion Evolution Through The Years

For years, Anna Kournikova absolutely dominated the world of tennis, but she was more than just a dab hand with a racket. Some sports stars manage to transcend into full-blown celebrities, though it doesn't happen very often. Kournikova was just 10 years old when she was profiled by The New York Times in 1992 and was given more attention than most as she went from child prodigy to title-winning tennis pro. The Russian-born beauty became more than just an athlete. She was one of the "It" girls of the 2000s, turning heads for her fashion choices way before she started dating singer Enrique Iglesias.

Kournikova's evolution from a sweet, determined child star in a shell suit to a grown woman with a penchant for sultry dresses is fascinating to behold, but it's her transition into parenthood and post-retirement life that really wins the trophy. Her style changed to accommodate the different phases in her life, but make no mistake, Kournikova has always managed to win when it comes to staying true to her aesthetic.

She may do less partying than she did in the early '00s, but Kournikova still pulls it out of the bag when it comes to photoshoots and sweet family photos alike.

Believe it or not, there are some '90s fashion trends that are coming back in style. While some of them we can get down with (hello tiny purses and crop tees), some are best left firmly in the past. Shell suits were incredibly popular back then, but when we look back at them now, it's hard to see why we loved them so much. No one who grew up in the '90s got away from this trend unscathed, not even Anna Kournikova. In 1994, she was already making her mark in tennis, as she scooped the trophy at the Les Petits As competition.

The prestigious competition sees players up to the age of 14 compete for a shot at the title. While it's not quite Wimbledon, some of the best tennis stars have cut their teeth there — Lindsay Davenport was a finalist in 1990. While we should look back on this moment in time as a turning point in Kournikova's career, we can't help but focus on the fashion more than anything else.

The shell suit is a testament to the times, absolutely swamping her tiny frame as she raised the trophy above her head. The dizzying blue and purple of the suit is enough for Kournikova's smiling face to become part of the background. But hey, if nothing else, it looks comfortable.

The next two years that followed Anna Kournikova's Les Petits As win were just as thrilling. In 1995, she scooped the coveted title of the ITF Junior World Champion. That's no mean feat, as she beat out plenty of other talented young hopefuls to scoop the prize. In 1996, she attended the ITF World Champions Dinner at the French Open wearing a simple black button-down dress. Her trademark blond locks were worn loose and straight, and she posed for photos as she tucked her hair behind her ear, holding her ITF trophy. At this point, she was days away from being 15, but signs of her future style were beginning to emerge. 

In the years that followed, Kournikova started to grow up and play around with her personal style more, but two things from this era remained the same for a long time: her love of monochrome and her blond hair. While some stars may play around with their hair color and use their youth to experiment, Kournikova was fairly certain of her aesthetic from an early age. 

The tennis star's style would simply evolve and become more sultry as she entered womanhood. But for this era in 1996, Kournikova looked wholesome, healthy, and girl-next-door, proving she was a great role model for young athletes across the globe. 

By the year 2000, Anna Kournikova wasn't just a tennis whizz who owned the matches she played; she was also a bonafide celebrity. The media was just as interested in her personal life as they were in her athletic ability, perhaps even more so. After all, she was a stunning 18-year-old who reportedly had a net worth of $75 million thanks to her savvy sponsorship deals and tournament wins. She was also allegedly engaged to fellow sports star Pavel Bure from the Florida Panthers.

Around that time, Kournikova's mother was also coming under fire for her "fiery style" with the New York Post claiming that Alla Kournikova was responsible for the breakdown of her daughter's relationship with Bure. As for Kournikova, she kept busy playing her sport and attending events, like the Sanex WTA Awards at Club Level in Miami, Florida, in March. The athlete showed off her lean physique and golden tan by wearing a black crochet two-piece outfit and a leopard print bra.

She paired the look with chunky heels, wearing her blond hair slightly messy and loose. It was a striking look for someone so young, but Kournikova was ready to own her aesthetic and have fun with 2000s trends as she progressed into the millennium.

In the early 2000s, Anna Kournikova made it clear that she wasn't just a sports star with a pretty face. She was an international sex symbol. In 2003, she posed for Sports Illustrated's infamous swimsuit issue, wearing a white bikini as she frolicked in the sand at El Conquistador Resort on Isla Palominos, Puerto Rico. By now, she was just as famous for her striking outfits and photoshoots as she was for her tennis career. The chances are that during this period, even if you weren't a fan of the sport, you knew Kournikova. 

In 2004, she attended the Anniversary Party of Light and Caramel at The Bellagio in Las Vegas, wearing black leather pants, a very of-the-moment matching purse, and a cropped white top with spaghetti straps. The star accentuated her outfit with a long silver necklace and big hoops, making her look as though she belonged in a hip-hop music video. Her beaming smile wasn't just down to her popularity at the time, but her longtime love. Anna Kournikova's relationship with Enrique Iglesias was in full bloom by this point, with the pair finding love on the set of Iglesias' music video for "Escape" in 2001. 

Whether Iglesias' popstar status influenced Kournikova's fashion during this era is up for debate, but she already had quite a strong sense of style before she started dating the famous singer.

It's clear, even now, that Anna Kournikova lives a lavish life. But back in the 2000s, it was even more prevalent. The tennis pro was often spotted at different events, rocking the red carpet solo and wearing some impressive outfits. However, monochrome was often her trademark. Kournikova sported black and white outfits regularly, rarely stepping out of her comfort zone to wear something bold and bright. When she did dare to wear something colorful, it turned heads. In 2006, she attended the Andre Agassi Charitable Foundation's 11th Annual "Grand Slam for Children" Fundraiser at the MGM Grand Garden Arena in Las Vegas — and she went all out.

Kournikova wore a breathtaking multi-colored floor-length dress that showed off her svelte frame while also keeping things PG. The ethereal gown made her look like a mermaid coming to shore, with her blond hair worn in loose waves around her shoulders. Kournikova paired the dress with simple, strappy gold sandals, and as far as a charity gala look goes, she knocked it out of the park. Other stars in attendance that night included Michael Caine and his wife, Shakira, and Sarah McLachlan.

While everyone dolled up for the occasion, Kournikova really stood out with this departure from her normal, darker wardrobe.

If you haven't guessed, Anna Kournikova spent a lot of time in Las Vegas in the '00s, attending events and having a good time. As a young female celebrity, there isn't a better place to be. Kournikova was such an icon by this point that she even participated in the 2009 USO Holiday Tour, performing alongside comedians like Dave Attell for troops based in Afghanistan. Her status as a pop culture phenomenon was well and truly cemented. However, Kournikova's style remained demure and sultry, though it was getting slightly more refined as the 2010s began to roll around. 

In this snap taken in Las Vegas in 2009 at the HardBat Classic and Killerspin All-Star Table Tennis Tournie, the blond beauty can be seen wearing a skin-tight bronze satin dress with matching peep-toe heels. Whether she intentionally matched the brown décor isn't known, but Kournikova looks like a breath of fresh air in an otherwise fairly grubby background. This well-put-together outfit made her look like a supermodel who wouldn't look amiss sitting next to Kate Moss. 

Interestingly, Kournikova made headlines just a couple of days after the event for reportedly getting into a bar fight. Luckily for her, no photos of the altercation exist.

Anyone who lived through the 2010s remembers just how popular tailored shorts became. Suddenly, everyone from Taylor Swift to Meghan Markle was wearing shorts on a night out. Tailoring became a huge trend, bringing office wear into nightclubs and giving us all a smart-chic aesthetic that we couldn't get away from in a hurry. Anna Kournikova was also a big fan of the look, which worked perfectly with her love of monochrome. In 2010, she attended the Grand Opening of JW Marriott Marquis in Miami, Florida, and wore sleek shorts with a matching blazer.

This time, she brought a little sparkle to the outfit with her black top, giving her a little more of a playful vibe. Her dark eye makeup and blond tresses remained the same, but it was good to see a little bit of light-catching glitter thrown into the mix. By this point, Kournikova had been dating her Spanish beau, Enrique Iglesias, for almost 10 years. However, despite being officially coupled up, they rarely attended red-carpet events together, meaning Kournikova (and her outfits) steal the spotlight solo.

The stunning transformation of Anna Kournikova really amped up in the last decade. Although she actually retired from tennis at the young age of 21 in 2003, Kournikova continued to make a splash in the public eye for years afterward. However, by the mid 2010s she had begun to live a relatively quiet life alongside Enrique Iglesias and was really spotted on red carpets. In fact, the most recent image of her attending a public event on Getty Images is 2014, when she was pictured watching the US Open. These days, if you want to catch a glimpse of what Kournikova is up to, the best place to turn to is her Instagram profile. 

In 2016, she posted a photograph of herself with two girls, presumably family members. While the sweet snap doesn't have a caption, it shows the former tennis pro eating an ice cream while wearing an outfit so far removed from her previous sultry event looks that it almost doesn't look like her. Kournikova's casual ensemble features ripped jeans and a white tank top with the American flag, although the stars have been removed and replaced with a heart.

She wears a simple black heart necklace, multiple bangles, and finishes off the look with white nail polish and big, chunky white sneakers.

Even retired athletes are worthy of attention. In 2019, Anna Kournikova posed up a storm for the Russian edition of Cosmopolitan, proving that she has what it takes to turn heads and be the belle of the ball. The cover story featured multiple photographs of Kournikova taken by Marc Baptiste, and in each snap, she wore different colorful outfits. The fresh-faced star — who looked like she hadn't aged a day since the 2000s — shared a boomerang on Instagram of herself on the day, wearing an orange dress with a very low-cut neckline. 

She wore simple gold jewelry to highlight her flawless tan, but more than anything, Kournikova looked as healthy and in shape as she was when she was 21. The only slight difference fans may have noticed during this shoot is that for some photos, Kournikova waved her hair more than she usually did, giving off a surfer-chic look that worked incredibly well with the bold and colorful theme. 

It's interesting to note that by this point, Kournikova had welcomed her first children, twins that came along in 2017. Not long after this shoot in 2020, she would welcome their third child.

For the photoshoot with Cosmopolitan Russia, Anna Kournikova wowed readers by wearing a stunning green maxi dress. The beautiful emerald gown had ruching from the halterneck top that flowed down to the ground, giving Kournikova the appearance of a Greek goddess. In the photo she shared on her Instagram, the former professional athlete turned her face to the sun while closing her eyes. She wore gold eyeshadow and nude lipstick, while her silver accessories harked back to her '00s penchant for hoops. 

It's an undoubtedly stunning look that is both mature and playful. Two decades ago, Kournikova may have considered this a little too demure, as she often preferred to flash a little flesh and show off her tanned legs. There are some fashion trends from the '00s that deserve to make a comeback, and given this photo, maybe bronzer is top of the list. 

After all, a healthy glow can work wonders, and Kournikova, in her late 30s when this photo was taken in 2019, looked just as youthful as she did when she was hitting the town in Vegas as a young woman. 

Since the 2010s, Anna Kournikova has taken a step back from the spotlight. As a result of her desire for privacy, not much is known about Enrique Iglesias and Anna Kournikova's three children. However, every now and then, we get a little glimpse into their lives when one of their parents shares a snap on Instagram. In 2022, Kournikova posted a photo of herself and Iglesias playing with their kids. Her playful mom style included an all-black outfit, harking back to her love of monochrome, but it included a sweet twist. 

Kournikova wore her hair in a high ponytail and accessorized it with a baby pink bow. She kept her jewelry simple with a white pearl necklace and a cross chain and small stud earrings. But it's the kids who really stole the fashion show here, with both daughters in cute red and pink outfits and their son in a dapper button-down shirt. Iglesias also opted for casual attire, wearing an Adidas hoodie, combat pants, a scarf, and a baseball cap. 

Kournikova had kept a low profile since posting this photo, however, something tells us her fashion evolution isn't over just yet.