Kylie Jenner questions her dress at 2025 Golden Globes: ‘Should I have looked like this with my t***s out?’

American entrepreneur Kylie Jenner may consistently top best-dressed lists, but even she has her moments of self-doubt. In the season 6 finale of popular reality TV show The Kardashians, the 27-year-old beauty mogul opened up about her mixed feelings after attending the Golden Globes with boyfriend Timothée Chalamet in January this year.

The moment came in a post-credits scene, where Kylie called her mom, Kris Jenner, to debrief after the glitzy evening. “Should I have looked like this at the Golden Globes with my t**s out?” she asked bluntly, referring to her daring outfit. Without missing a beat, Kris reassured her daughter: “Yes. You have to wear your best dress to every function you go to no matter what.”

For the red carpet of the popular awards ceremony, Kylie wore wore a vintage silver chainmail gown from Atelier Versace — a bold, body-hugging piece that drew comparisons to the iconic dress worn by Elizabeth Hurley at the 1999 CFDA Awards. The shimmering metallic fabric, delicate and intricate, highlighted Kylie’s silhouette while maintaining an edge. She kept her overall look understated yet elegant, styling her black hair in soft curls and accessorizing with sparkling Lorraine Schwartz jewelry.

But the show-stopping dress wasn’t without its challenges. At some point during the night, Kylie appeared to suffer a minor wardrobe malfunction — a small section of the chainmail reportedly ripped, creating a visible hole in the otherwise seamless ensemble.

Even so, Kris’s advice didn’t stop at outfit confidence. She followed up with a classic Jenner-ism: “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.” Kylie, amused, replied with a simple “okay.”

The exchange offered a rare glimpse into the more vulnerable, human side of Kylie’s fashion-forward persona — a reminder that even A-listers occasionally question their choices once the cameras stop flashing.