Anna Kournikova Outfits That Completely Missed The Mark

You wouldn't be alone if you were wondering what happened to Anna Kournikova since she retired from professional tennis in 2003 at the age of 21. Well, the Russian-born tennis star lives a rather lavish life and jet-sets around the world. She also participates in a number of charitable organizations and is mother to her and partner Enrique Iglesias' three children — twins Nicholas and Lucy, born 2017, and Mary, born 2020.

Kournikova actively documents her life on Instagram, sharing details of her workouts, posting pics of her family, and uploading plenty of selfies showing off her fashion prowess, which has definitely evolved over the years. For the most part, she wears a lot of the modern-day mom uniform: athleisure. For her mom-off-duty looks, she frequently opts for form-fitting leggings or jeans paired with chic tops. She loves to rock a heeled bootie, and her handbag game is strong, with Balenciaga and Hermes purses making it into her rotation. Like all of us, though, she's had some off days and worn a few cringeworthy outfits that completely missed the mark, from back when she was a child tennis prodigy to her appearances on the tennis court — and even the red carpet.

It's well-known that there's a lot of protocol surrounding tennis' grandest tournament, Wimbledon, from the rules about sitting in the royal box to what players can wear. One such example is that they have to wear predominantly white. According to Athleta, the color fits "with the elegant air of Wimbledon's luxury." It's also more forgiving of sweat stains than other colors, further perpetuating Wimbledon's unsoiled, aristocratic vibe.

So, was Anna Kournikova up to standard in 2002 when she wore an all-white Adidas ensemble? Surprisingly, not at first. And it's not because some thought her outfit was too revealing — there's nothing dictating how risqué a player's wardrobe may or may not look in the tournament's official rules. No, she was instead asked to change her undershorts. According to the BBC, the pro wore black shorts beneath her skirt, a no-no at the time. (This rule was changed for the 2023 season, when female players were granted the right to wear darker shorts to accommodate concerns of players on their periods.) The BBC reported that Kournikova borrowed a pair of white shorts from her coach so she could continue playing.

Though Anna Kournikova never won a trophy in her singles tennis career, she was awarded the coveted title of FHM Magazine's "sexiest woman alive" in 2002. And it seems that both Kournikova and her team were determined to uphold this sex-symbol image even as her tennis career slowed. One example of the more revealing outfits she donned during this era occurred at the 2003 New York premiere of "Once Upon a Time in Mexico." Accompanying boyfriend Enrique Iglesias, who co-starred in the film, Kournikova wore a white bra-style top and sarong-style skirt that closed with a string tie at the hip, revealing her entire left leg.

While the look is definitely flattering on the tennis star, we argue this moment missed the mark because she was attending a film premiere, not an outing to a Vegas nightclub. Other red carpet attendees were dressed more appropriately for the occasion, including Salma Hayek in a little black dress and Vanessa Paradis (there with Johnny Depp) in a '20s-inspired Chanel dress.

If there's one thing Anna Kournikova is known for looks-wise, it's her long blonde hair, as well as her signature style when she was on the court: the long, braided ponytail. Vogue even called the hairstyle "summer's easiest up-do" in 2024, pointing out that it inspired Zendaya on her "Challengers" promo tour.

But one time when Kournikova's hair missed the mark was with this padded headband she wore in her youth (she's pictured here with her father, Sergei Kournikov, a wrestling champion and professor). When we see padded headbands, we think Hillary Clinton in the '90s and prissy Blair Waldorf on "Gossip Girl." Vogue even tried to espouse that the look was back in 2023 thanks to Jennifer Lawrence and Sofia Richie Grainge sporting the accessory. But it appears the puffed-up hairpiece hasn't succeeded in taking over the mainstream, nor has Kournikova been spotted wearing a padded headband ever again.

In October 2003, then-22-year-old Anna Kournikova attended the World Music Awards. The event, held in the plush principality of Monaco, honors the best-selling and "most popular recording artists from every continent," per the World Music Awards website. Unfortunately, we have to say that Kournikova's outfit for the event didn't quite rise to the occasion.

At this point in her career, though she was retired from professional tennis, she was still making money from endorsements (Adidas, Omega, and Berlei among them), but you wouldn't know it from this ensemble. It looks like something she might have grabbed off the sale rack at a fast-fashion retailer geared toward teens. The ruched, off-the-shoulder pink top looks thin and cheap, while the tattered white denim mini skirt feels too casual for an awards ceremony — especially one on a global scale. She finished with the baffling footwear choice of pink snakeskin cowboy boots. While the look might have been fun for a night out with friends, it doesn't strike us as special enough for an international red carpet. Thankfully, more than 20 years later, Kournikova's style sense has come a long way, and these fashion mishaps are a thing of the past.