The Most Inappropriate Outfits Anna Kournikova Has Ever Worn

Professional athletes have plenty to be proud of: championships won, records broken, and personal bests redefined again and again. Yet, certain players take on even bigger reputations in the public eye. Anna Kournikova is a prime example. Despite her tennis skills, Kournikova came out of her sports career known as much for her looks as for her game. The tennis star, one of the it-girls of the early noughties, started as a kid athlete and ended up as a model and spokeswoman with multiple high-value brand deals.

It's no wonder, then, that Anna Kournikova underwent a gorgeous transformation during her years in the spotlight. However, the tennis star's time in the sun was also subject to a lot of scrutiny and criticism, including sartorial critiques. Like pretty much any celeb who survived the early 2000s, Kournikova made some now-cringe-worthy fashion choices, from belly-baring outfits at the wrong events to morally dubious fashion picks that wouldn't fly today.

In an ideal world, female athletes would be recognized more for how they play than for what they wear while doing it. Still, certain ensembles can't help but raise questions, like the sporty separates Anna Kournikova chose for Arthur Ashe Kids' Day in 2003. This charitable event, which raises money for the National Junior Tennis League, bridges the gap between pint-sized enthusiasts and tennis pros through various sports clinics and kid-friendly activities.

In short, it's like a special exhibition for young tennis fans. So, why, one might ask, did Kournikova decide to expose extra swathes of skin with a short-cropped white sports top and a low-riding Adidas tennis skirt? In 2003, Kournikova was at the end of her professional tennis career and was understandably more focused on her modeling and public image. But while slinky, midriff-baring styles may have been in vogue for pop starlets of the era, a family-oriented tennis event doesn't feel like the right place to flaunt your sex appeal.

Also in 2003, Anna Kournikova enjoyed the benefits of her star status by attending high-profile events like the New York premiere of "Once Upon a Time in Mexico." However, it seems she hadn't yet mastered the nuances of red-carpet styling, as Kournikova showed up to the premiere in itty-bitty separates that felt far too trendy and casual for the occasion. Arriving alongside then-boyfriend and now-husband Enrique Iglesias, Kournikova walked the red carpet in a plunging white bra top and a matching wrap skirt that might as well have been a swimsuit cover-up. The look was extremely beachy and completely informal, missing the mark for a star-studded event.

Now, if the premiere had been in Miami, we'd at least give the ensemble credit for fitting the climate, but New York in September is a far cry from Florida in July. What's more, who wears such an outfit to the movie theater, where temperatures are notoriously chilly? We hope Iglesias was at least keeping her warm during the film — we're getting cold just thinking about Kournikova's thin clothes against all of that A/C.

When Anna Kournikova was playing in tournaments, she only had so much latitude in her wardrobe. But in 2000, she had the chance to attend a charity tennis match at Buckingham Palace as a spectator rather than a player, leaving her fashion options wide open. Unfortunately, Kournikova flubbed the opportunity anyway.

Watching a match at the seat of the British monarchy might seem like the perfect time to show off some classic tenniscore couture, but Kournikova inexplicably didn't dress up to the royal standard of the event. Instead, she once again chose to go the chill and flirty route by donning a clingy silk halter dress by Dior. While not a cheap look, it didn't seem to fit the theme or venue of the event. Already giving off an aesthetic that was more nightclub than country club, the garment was rendered even more casual by its faux-denim print, putting Kournikova's styling miles away from any semblance of the aristocratic refinement repped by other guests.

In November 2000, Anna Kournikova risked putting herself on the wrong side of history when she gallivanted around New York City in a long fur coat. The tennis star was papped in the brown coat strolling Times Square on the arm of Stephen Urquhart, president of Omega Watches. It had just been announced that Kournikova was entering a promotional partnership with the brand, with sources at the time suggesting that the deal would net her six figures annually. With Omega being a known luxury label, it could be argued that pulling out an expensive mink coat was on-brand for the partnership's unveiling, so at least Kournikova was event-appropriate for once. However, most fashionistas know by now that fur couture has seen a precipitous fall from grace.

These days, many heavy-hitting fashion houses, including Gucci and Chanel, have abandoned the use of fur outright. Why not, when wearing fur raises ethical questions and there are many synthetic alternatives that deliver the look without the controversy? To be fair to Kournikova, the look itself is still popular — faux-fur coats being the signature outerwear trend of 2024's mob wife aesthetic was proof of that. But "faux" is the key word to avoid scorn in modern fashion circles. Wearing real fur still isn't totally unheard of, but it means running the risk of moral judgment.

Fur coats weren't the only questionable clothes that Anna Kournikova wore in the name of her partnership with Omega watches. At a reception held by the brand at the Parisian nightclub Man Ray in 2001, Kournikova showed off the luxury accessories in a curious array of costumes. During the presentation, she dressed up in several glitzy, super-sexy versions of an Indian lehenga choli (a three-piece outfit consisting of a lengthy skirt, a blouse or top, and a shawl). What did these ensembles have to do with Omega watches, which are from Switzerland; the event, which was in France; or the tennis star herself, who hails from Russia? The connection is unclear, which makes the use of these cultural outfits seem suspicious in retrospect.

At the turn of the millennium, society hadn't quite figured out where to draw a tasteful line regarding cultural appropriation, and it shows. Even global pop icons got in trouble for similar costuming — a 2009 Indian-inspired concert 'fit still counts among Britney Spears' most inappropriate outfits yet. So, if Kournikova now looks back at ill-advised outfits like these and cringes, at least she's in good company.