Kylie Jenner walked the Victoria’s Secret runway for the first time on October 18, 2026, and she did it wearing the brand’s Fantasy Bra, a diamond-covered piece reportedly valued at $50 million. The Kylie Jenner Victoria’s Secret moment grabbed headlines, but insiders say not every model backstage was cheering.
The 29-year-old founder of Kylie Cosmetics had never appeared in the show before. That alone made her selection for its most prestigious look a surprise. According to sources quoted by the Daily Mail, her mother, Kris Jenner, had a hand in making it happen.
A bra with a long line of famous wearers
For anyone who watched the show on TV in the late 1990s and 2000s, the Fantasy Bra was the night’s main event. One model, almost always a top Angel, would take the runway in a jeweled bra worth more than most houses.
Claudia Schiffer wore the first one in 1996, a piece valued at $1 million. Gisele Bündchen carried a $12.5 million version in 2005. Heidi Klum, Tyra Banks and Adriana Lima all had their turns. Candice Swanepoel wore it in 2013, and Elsa Hosk’s 2018 bra was reportedly valued at $1 million.
Jenner’s version beats them all on price. Made with jeweler Jacob & Co., it carries around 4,410 natural diamonds with a combined weight of 1,373.39 carats. It has been described as the most expensive Fantasy Bra to date.
The jump is striking. Hosk’s bra in 2018 was valued at the same $1 million as Schiffer’s original 22 years earlier. Jenner’s is worth fifty times that.
The choice also says something about where Victoria’s Secret is now. The show went off the air after its 2018 edition, as ratings slid and critics called its image dated, and it came back in 2024 in a revamped format. Giving the brand’s signature piece to a celebrity with an enormous social following, rather than a career runway model, fits that reset.
Adam Selman, the company’s chief creative officer, told Vogue that Jenner was picked because her reach goes well beyond fashion. He framed it as a chance to put the brand’s most extravagant creation on someone with a huge audience and wide cultural pull.
How Kris Jenner reportedly helped seal the deal
An insider told the Daily Mail that Kris was thrilled her youngest daughter landed the spotlight and pushed for the walk to feel like a “princess moment.” “Kris can sure work a deal,” the source said.
Kris has managed her children’s careers for years and has a reputation for turning a headline into a business opportunity. This one came with a runway, a global audience and a $50 million centerpiece.
Kylie was said to be flattered when the brand reached out, and she reportedly agreed straight away. The same source claimed she also saw the obvious upside for her cosmetics business.
Her sister Kendall Jenner, a runway regular for more than a decade, couldn’t join her. Kendall is tied to Intimissimi, a rival lingerie label. According to the insider, she urged Kylie to say yes and backed the decision, which reportedly helped Kylie feel at ease in a slot usually reserved for established Angels.
Some veteran models were reportedly not impressed
Jenner’s casting was reportedly kept quiet for months. When some longtime models found out who would wear the Fantasy Bra, sources said they were left “speechless.”
One insider claimed several of the “old-school” models were unhappy that a newcomer had become the focus of the night. The source put it bluntly, describing Kylie as a billionaire cosmetics mogul rather than a model, and suggested some veterans wondered why the honor didn’t go to experienced runway talent.
The insider singled out Swanepoel and Hosk, both past Fantasy Bra wearers, claiming neither looked especially happy during the show. That is one source’s reading of their expressions. Neither model has commented, and nothing has been confirmed.
Both women earned their Fantasy Bra walks after years on the Victoria’s Secret runway. Jenner got hers on her first appearance.
The same source predicted the veterans would keep any frustration to themselves. They understood, the insider said, how much attention Jenner’s appearance would bring.
Plenty of support in the room
If there was tension backstage, Jenner had no shortage of allies out front. Kris sat in the audience along with Timothée Chalamet, Kylie’s boyfriend, who was reportedly seen applauding as she walked.
Gigi and Bella Hadid, both friends of Kylie’s, also walked in the show, and singer Tate McRae performed. The insider also claimed that model Irina Shayk was fine with the whole thing.
For now, every report of friction traces back to unnamed sources. What’s on the record is the bra itself: 1,373.39 carats of natural diamonds, worn by a woman who had never set foot on the Victoria’s Secret runway before October 18.
