Kylie Jenner made her Victoria’s Secret runway debut on October 18, 2026, but her appearance reportedly came with a generous helping of backstage tension.
Keep reading to learn more.
29-year-old beauty mogul Kylie Jenner didn’t just walk in the Victoria’s Secret show. She also wore the brand’s coveted Fantasy Bra; a diamond-covered piece reportedly worth $50 million.
While Kylie’s headline-making moment attracted plenty of attention, sources claimed some longtime Victoria’s Secret models were less than impressed with the decision to give her the spotlight.
And according to one insider, Kris Jenner may have helped make the whole thing happen.
Kylie reportedly got the Fantasy Bra after Kris Jenner helped broker the deal
The Fantasy Bra has traditionally been worn by some of Victoria’s Secret’s most recognizable models, including Heidi Klum, Tyra Banks, Gisele Bündchen, Claudia Schiffer, and Adriana Lima.
But this year, the honor reportedly went to Kylie, who had never walked in a Victoria’s Secret show before.
A source told the Daily Mail that Kris Jenner was delighted her youngest daughter had landed the high-profile moment, and allegedly helped turn it into a “princess moment.”
“Of course, Kris Jenner loved that Kylie was wearing the diamond bra. Kris can sure work a deal,” the source said.
The insider claimed Kris wanted Kylie’s appearance to be especially memorable, adding that she reportedly pushed for the moment to feel like a major event.
Kylie, meanwhile, was said to be “flattered” when Victoria’s Secret approached her and agreed to take part right away.
The source also claimed Kylie understood the publicity could benefit her cosmetics business.
Kylie reportedly had Kendall Jenner’s support
Kylie’s older sister, Kendall Jenner, is a longtime runway model, but she reportedly couldn’t take part because of her association with Intimissimi, a competing lingerie brand.
According to the insider, Kendall encouraged Kylie to do the show and supported her decision.
That family backing reportedly helped Kylie feel comfortable stepping into a role usually associated with established Victoria’s Secret Angels.
But not everyone backstage was said to be celebrating.
Some veteran models were reportedly unhappy that Kylie became the center of attention
Kylie’s selection was reportedly kept under wraps for months. When some longtime models learned she had been chosen for the Fantasy Bra, sources claimed they were “speechless.”
One insider told the Daily Mail that certain veteran models weren’t pleased to see Kylie take the spotlight.
“Some of the old-school models were not thrilled that Kylie was the center of attention,” the source said.
The insider suggested that some established stars may have felt frustrated watching a younger celebrity receive such a prominent moment.
“Kylie is not a model; she’s a billionaire cosmetics mogul,” the source added, claiming some veterans may have wondered why she was chosen over experienced runway talent.
The source specifically mentioned Candice Swanepoel, who wore a Fantasy Bra in 2013, and Elsa Hosk, who wore one in 2018.
The insider claimed the two models didn’t appear especially happy during the show. However, those alleged reactions are based on a source’s interpretation, there has been no confirmation from either model.
The same source suggested the veterans were unlikely to publicly criticize Kylie, saying they understood how much attention her appearance would generate.
Kylie still had plenty of familiar faces cheering her on
Despite the alleged backstage friction, Kylie reportedly had a strong support system around her.
Her mother, Kris, and boyfriend Timothée Chalamet were in the audience, with Chalamet reportedly applauding as she walked.
Her friends Gigi and Bella Hadid were also part of the show, while singer Tate McRae performed.
The insider also claimed that model Irina Shayk was “cool with it.”
So while some veterans may reportedly have questioned the decision, Kylie wasn’t short on friends and supporters during her debut.
The $50 million Fantasy Bra was covered in thousands of diamonds
The show’s Fantasy Bra was created in partnership with luxury jewelry company Jacob & Co.
According to the details provided about the piece, it featured around 4,410 natural diamonds, with a total weight of 1,373.39 carats.
Victoria’s Secret chief creative officer Adam Selman explained to Vogue that Kylie was chosen because her influence extends beyond fashion.
He described the pairing as an opportunity to put the extravagant piece on someone with a huge following and broad cultural impact.
The Fantasy Bra first appeared in 1996, when Claudia Schiffer wore a version valued at $1 million. Gisele Bündchen later wore a $12.5 million design in 2005, while Elsa Hosk’s 2018 version was reportedly valued at $1 million.
Kylie’s bra was described as the most expensive one to date.
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