Kylie Jenner is showing off what her mama gave her with her blessing.
Three months after the Kylie Cosmetics founder dazzled at the 2025 Golden Globes in a silver vintage Versace gown alongside her boyfriend Timothée Chalamet, the Kardashians finale episode shared insight into her uneasy feelings about her look after the event.
While Kris Jenner was filming her confessional interview, which aired as a post-credits scene in the April 10 episode, Kylie gave her mom a call, where she asked, “Should I have looked like this at the Golden Globes with my t-ts out?”
But Kris—who is mom to Kourtney Kardashian, 45, Kim Kardashian, 44, Khloe Kardashian, 40, Rob Kardashian Jr., 37, with the late Robert Kardashian and Kendall Jenner, 29, and Kylie, 27,with ex Caitlyn Jenner—was quick to shut down her concerns.
“Yes,” she replied. “You have to wear your best dress to every function you go to, no matter what.”
Kylie turned heads at the 82nd annual award show—where Timothée was nominated in the Best Actor in a Motion Picture – Drama for his role in A Complete Unknown—with her risqué backless chainmail gown.
And for the Kardashian-Jenner matriarch, she means wearing your best no matter what.
“It’s like I tell you,” Kris continued, “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.”
Her advice appeared to soothe Kylie, who simply said, “OK,” before hanging up the call.
Although the youngest Jenner was apprehensive about her appearance during the ceremony, she’s always down to push fashion boundaries. Most recently, she dropped jaws while showing off the launch of her new latex dresses, which she teased she “would wear this outfit to pick up my kids from school.”
As for the outfit itself? Kylie—who shares kids Stormi, 7, and Aire, 3, with ex Travis Scott—donned a bright red skintight gown that prominently displayed her cleavage.
While the reality star loves trying out new looks, she admitted that there’s pressure when it comes to showing out.
“It’s hard to have so many iconic looks because you’re always trying to outdo the last one, but I think just remaining myself, being classic, and wearing what makes me feel great is where my head’s at right now,” she explained to Elle in October. “I think I’m actually going in the opposite direction. I’ve definitely had some moments of quiet luxury, as they would say, but I’m always experimenting.”
In many ways, she’s attributed her style evolution to her journey as a mom.
“I haven’t had a baby in a few years,” she continued. “The first part of my twenties was having children, learning what my personal style was and then losing it—not knowing how to dress, gaining 60 pounds for both pregnancies. It took me a year to feel like myself again.”
As Kylie put it, “At 27, I feel more confident and more like myself than ever.”
Read on to keep up with Kylie’s iconic fashion evolution.
2008
Kylie attends Matrix at A Time for Heroes Celebrity Carnival just months before the Keeping up with the Kardashians series premiere.
2009
Kylie shows support for Selena Gomez‘s Kiss & Tell album by attending its release party.
2009
Kylie sports bangs at Wango Tango music festival in Los Angeles.
2010
Kylie is all smiles at the Taste Of Beverly Hills.
2010
Kylie attends Wango Tango festial for the second year in a row.
2011
Kylie attends the 2011 People’s Choice Awards in Los Angeles.
2012
Kylie attends the 2012 Teen Choice Awards just ahead of her 15th birthday.
2012
Kylie goes grunge at Jingle Ball 2012.
2013
Kylie vogues at the MTV Movie Awards.
2013
Kylie shows support for pal Justin Bieber at the Justin Bieber’s Believe premiere.
2014
King Kylie arrives at the 2014 Billboard Music Awards.
2014
Kylie walks the blue carpet at the 2014 Teen Choice Awards.
2015
Kylie is all grown up at GQ’s Grammys after party in 2015.
2015
Kylie brings back the bangs for a night at the 2015 MTV Video Music Awards.
2016
Suited up! Kylie sports a business casual vibe at Marie Claire‘s ‘Fresh Faces’ Party.
2016
Kylie walks her own red carpet at her 2016 charity event with SinfulColors.
2017
Kylie sports a two-piece ensemble at Marie Claire‘s Image Maker Awards 2017.
2017
Kylie goes blonde at the 2017 Met Gala.
2018
A year later, Kylie returned to her roots for an all-black look at the 2018 Met Gala, just months after welcoming her daughter Stormi with her now-ex Travis Scott.
2019
Kylie supports Travis at the premiere of Travis Scott: Look Mom I Can Fly.
2019
Kylie steps out in a Balmain jumpsuit at the 2019 Grammys.
2020
Kylie is feeling blue at the 2020 Vanity Fair Oscars Party.
2021
She’s on the move! Kylie leaves the Parsons Awards in 2021.
2022
Kylie steps out at the Baby2Baby gala months after welcoming her son Aire.
2023
Kylie is seeing red on the 2023 Met Gala red carpet.
2024
Kylie uses her seltzer Sprinter as the ultimate accessory while out and about in Los Angeles.
2025
Kylie teased her new collection of latex dresses, donning a low-cut red gown that she would wear “to pick up my kids from school,” business meetings or “the clurb.”
