Kylie Jenner Confuses Tennis Match For Playboy Cover Shoot In Inappropriate Outfit

It looks like Kylie Jenner didn't get the memo on dressing appropriately for watching a tennis match. Jenner and her boyfriend, Timothée Chalamet, were spotted packing on the PDA again while watching the BNP Paribas Open on March 9. In a video shared by the organization on X, formerly known as Twitter, one half of the couple dressed accordingly, but the other did not, and it was — you guessed it — Jenner. The beauty mogul had on a bright red button-down shirt tied at the waist, showing her bare midriff. The top was barely buttoned, and Jenner's cleavage was on full display. Meanwhile, Chalamet had on a reserved striped shirt with a white t-shirt underneath, looking relaxed yet suitable for tennis. He was also spotted wearing a zip-up Adidas sweatshirt.

According to Vogue, proper attire for a big tennis tournament, such as the U.S. Open, includes polo shirts, a breezy shirtdress, or a fresh white skirt worn with a preppy top. We're sure Jenner's pin-up look wouldn't make its list of chic tenniscore 'fits, but as we all know, "The Kardashians" star loves to turn heads with inappropriate looks, and some of Jenner's fashion choices have even generated controversy. 

Kylie Jenner loves to show skin, and her inappropriate 2025 Oscars dress turned heads for all the wrong reasons. As Timothée Chalamet's date, Jenner showed up in a custom-made black Miu Miu dress with a bedazzled bra top and cut-out midriff with just a strap wrapping around her stomach. When Jenner shared the look in an Instagram post, a fan commented, "Should be classy not naked." Another wrote, "She should have gone more classy than flashy, considering Timothy respected his art." One critic pointed out, "Great look but poor choice for the Oscars."

Jenner's racy Oscars outfit caught the eye of political commentator Megyn Kelly, who blasted the poor choice of dress. "Where were people's clothes?" she asked on her eponymous show. "She's wearing a bathing suit, which is right on course for the Kardashian/Jenners crowd," Kelly added. Jenner later changed to a different dress for the Vanity Fair party, but it wasn't any less revealing than her previous gown. The Ashi Studio frock featured a corset top and gave the illusion of an overall sheer look. We're sure Kelly, who has a history of wearing risqué outfits herself, would have had plenty to say about that as well.