Kylie Jenner is proof that stars are just like Us: She worries about showing too much cleavage.
Jenner, 27, had doubts about the low-cut dress she wore to the 2025 Golden Globe Awards in January, which she attended with her boyfriend and nominee Timothée Chalamet.
“Should I have looked like this at the Golden Globes with my tits out?” Kylie asked mom Kris Jenner over the phone on the Wednesday, April 9, episode of The Kardashians, referring to the Atelier Versace she wore to the awards show.
Ever supportive of her daughter, Kris offered her reassurance and advice. “Yes. You have to wear your best dress to every function you go to, no matter what,” she said definitively.
Related: Kylie Jenner Leaves Timothee Chalamet Out of Golden Globes Instagram Post
One of the most talked-about moments from the 2025 Golden Globes was undoubtedly Kylie Jenner spending the evening all over her actor boyfriend Timothée Chalamet — but if you ask Jenner herself, it was actually more of a girls’ night. On Monday, January 6, the model and reality star, 27, documented her night at the […]
The Kardashian-Jenner momager shared another one of her sartorial philosophies with her youngest: “It’s like I tell you. You have to wear matching lingerie because if you’re ever in an accident and you have to go to the hospital, you’re gonna have gorgeous lingerie on,” Kris said.
Her daughter, seemingly accustomed and convinced by the guidance, simply replied, “OK.”
Jenner made a notable entrance at the ceremony, appearing in the iconic dress from Donatella Versace’s Spring 1999 collection — a design Elizabeth Hurley famously wore in a lilac version to the 1999 CFDA/Vogue Fashion Awards with her then-boyfriend Hugh Grant.
(The former couple dated from 1987 to 2000, and they’ve since then have remained close; the Notting Hill actor is the godfather to his ex’s son Damian, 22, whom Hurley, 59, shares with Steve Bing.)
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Naked dresses were on everyone’s mind on Oscars night. When Hollywood’s favorites grace the Academy Awards red carpet— and the Vanity Fair Oscar Party — to take home a trophy and celebrate the best films of the year on Sunday, March 2, another highlight of the affair was seeing Hollywood’s biggest stars bring their fashion […]
Despite any potential pre-ceremony jitters, Kylie confidently continued her awards season appearances with Chalamet, 29, at the star-studded Hollywood events that followed, like the BAFTAs and Oscars, in similarly striking dresses that were widely considered red-carpet wins.
They consistently landed her on best-dressed lists, including the look she wore to the Globes.
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