Kylie Jenner is making a concerted effort to ensure that her fashion choices are under the spotlight. The founder of Kylie Cosmetics, who graced the 2025 award season red carpets alongside her beau, Timothée Chalamet, has recently shared intricate details about her captivating outfits from these star-studded events. Her ensemble for the 2025 Oscars, a chic creation by Miu Miu, and the vintage John Galliano getup that turned heads at the 2025 BAFTAs, stand out prominently.
For each of these outings, including her and Timothée’s red carpet debut at the prestigious 70th David di Donatello ceremony in Rome, Kylie opted for a black dress—a timeless classic that she couldn't resist. "It just sort of happened that way," admitted Kylie, who is the doting mother of Stormi, 7, and Aire, 3, whom she shares with Travis Scott, in an interview with Harper’s Bazaar published on May 29. "Even recently, I was like, 'I can't wear another black dress.' And then, of course, the most exquisite, breathtaking Schiaparelli black dress came along."
The Schiaparelli moment that the Kardashians star referenced was a stylish design featuring a plunging neckline, which she donned while accompanying Timothée to the David di Donatello ceremony, where he was honored with the award for Cinematic Excellence.
As for why Kylie chose black for each of her memorable moments with her beau, she explained that she didn't want to steal the show. "Although these are the most stunning, iconic gowns I've worn, I believe a black dress is, in the best way, not too attention-grabbing," she elaborated. "You can never go wrong with a black dress."
And while Kylie was confident in her little black dresses (LBDs), she did have a moment of uncertainty before stepping out with Timothée at the 2025 Golden Globes in a stunning silver vintage Versace gown. In a clip from the April 10 episode of the family's Hulu series, Kylie called her mom, Kris Jenner, asking, "Should I have looked like this at the Golden Globes with my boobs out?" Kris, giving her youngest daughter her seal of approval, exclaimed, "Yes. You have to wear your best dress to every function you attend, no matter what."
