We know Anna Kournikova knows how to dress, because she’s rocked some seriously on-point fashion over the years.
From her gorgeous, floaty, cut-out maxi dress at the Grand Slam for Children fundraiser in 2006 to her flirty, red mini dress with leopard-print peep-toe heels at the Cedars-Sinai Sports Spectacular the following year, she’s served looks that were total wins.
Fashion was clearly a passion of the star, too, because she regularly shared her OOTDs (outfit of the day) on Instagram in the mid-2010s before stepping back from the spotlight. But, just like tennis, with the hits come the misses, and this oft-stylish beauty has had her fair share of faults.
Anna Kournikova’s stunning transformation has included years of ensembles that just didn’t work, even though she told Elle in 2011 she tries to stick to the basics.
“My style is very basic. Most of the time, I mix black and white. I love leather jackets or tailored blazers,” she said. She’s shown that straying from her usual style doesn’t always work.
Anna Kournikova’s Today look was way too casual
When Anna Kournikova appeared on “Today” to promote “The Biggest Loser” in 2011, she was dressed way too casually. The beauty wore dark blue jeans with a dark gray, slouchy, quarter zip sweatshirt over a black top and chunky, gray sneakers that resembled hiking boots.
The tennis star was dressed like she was going on a hike, not appearing one of the country’s biggest TV shows that shoots in the middle of one of the most cosmopolitan places in the world, New York City.
Particularly while sitting opposite co-hosts Hoda Kotb and Kathie Lee Gifford, who were donning polished, structured dresses and pumps, Kournikova’s understated style felt out of place.
Though we can understand why Kournikova wanted to dress a little sportier to promote the weight loss show, a few small tweaks would have instantly upgraded her outfit.
Swapping her bootcut blue jeans for black skinny jeans (a big trend at the time) would have instantly made the casual look dressier. Adding some simple heels would have put her ensemble on par with Kotb and Gifford’s style vibe, too.
We know Kournikova isn’t afraid of heels, as she’s worn them countless times, and told Elle, “I’m the kind of girl who goes with really high shoes or flip flops. I don’t do in between.” But if she wanted more comfort, athletic ballet flats would have been a more fashion-forward, yet sporty, choice.