Kylie Jenner Just Stole the Victoria’s Secret Show in a $50 Million Fantasy Bra
The beauty mogul made her surprise Angel debut with the priciest Fantasy Bra in Victoria’s Secret history — while Timothée Chalamet watched from the audience beside Kris Jenner.
Kylie Jenner has spent years perfecting the art of the entrance, but Sunday night’s Victoria’s Secret Fashion Show moment still managed to arrive with a little shock value. The beauty mogul appeared on the runway for the first time in the brand’s most loaded piece of lingerie history: a Fantasy Bra valued at $50 million.
Because apparently a regular runway debut would have been too quiet.
Jenner’s surprise walk instantly turned the annual lingerie spectacle into a full Kardashian-Jenner family event. In the audience, watching from a prime seat, were her boyfriend, Timothée Chalamet, her mother and professional spectacle architect Kris Jenner, and Kris’ longtime beau, Corey Gamble. The visual was almost aggressively on-brand: Kylie in diamonds, Timothée looking on, and Kris positioned close enough to take in every camera flash.
The bra was less accessory, more infrastructure
The Fantasy Bra is not a costume detail you casually throw on before heading out the door. This year’s version is the first Victoria’s Secret Fantasy Bra since 2018, and according to Vogue and jeweler Jacob Arabo of Jacob & Co., it is the most expensive one ever made.
The centerpiece is a yellow diamond valued at $22 million. Around it: more than 4,400 additional diamonds, arranged in nearly every cut imaginable, including pear, heart, round, oval and marquise. The design comes from Jacob & Co.’s Rare Touch Jewelry Collection, which is built around the idea that precious metal can move with the body like fabric.
That is a very elegant way of saying the bra was engineered to sparkle from every possible angle.
Jenner paired the diamond-heavy look with a peekaboo thong, keeping the overall styling firmly in Victoria’s Secret’s familiar language of glitter, skin and theatrical confidence. But the real headline was the scale of the jewel itself. At $50 million, it makes the traditional “statement accessory” feel almost quaint. This was not a finishing touch. This was the plot.
Kylie is not a runway regular — which made the reveal land harder
Jenner is no stranger to cameras, campaigns or a strategically timed glam moment, but she has never been the most consistent runway presence in the family. Her first runway appearance came in 2011 for Avril Lavigne’s former label, Abbey Dawn. Two years later, she walked alongside Kendall Jenner for Sherri Hill and The Heart Truth’s Red Dress Collection.
Her more recent runway appearance was a considerably more polished affair: Jenner closed Coperni’s spring 2025 show at Disneyland Paris in an elegant strapless ballgown. That appearance played like a fashion-world cameo. Sunday night felt more like a coronation.
There is also a neat little family loop here. Kendall has walked in the Victoria’s Secret Fashion Show three times — in 2015, 2016 and 2018 — though she was absent from this year’s glitter-heavy lineup. Kylie, meanwhile, had already flirted with the Angel fantasy long before she wore the real thing.
Back in 2015, the Kardashian-Jenner sisters dressed as Victoria’s Secret models for Halloween. Kylie borrowed Candice Swanepoel’s cutout catsuit, while Kim Kardashian posted a thank-you to the brand for sending “actual runway looks and real wings” for the occasion. A decade later, Kylie got the actual runway, the actual wings and, naturally, the most expensive bra in the room.
From Halloween fantasy to luxury lingerie crossover
The timing also makes sense for Jenner’s current fashion orbit. She has become increasingly comfortable moving between beauty mogul, campaign star and high-glamour fashion fixture. In February, she starred in a Skims campaign, putting her in the visual universe of Kim Kardashian’s lingerie and shapewear empire.
Now she has added Victoria’s Secret to the résumé, which gives the moment a pleasingly competitive family undertone without requiring anyone to say the quiet part out loud. Kim has Skims. Kendall has the established Victoria’s Secret runway history. Kylie arrived wearing $50 million in diamonds and made sure her debut could not be mistaken for a casual guest appearance.
That is the Jenner method at its most efficient: show up less often, but make the appearance impossible to discuss as merely normal.
Jenner’s presence also helped make the 2026 show feel like the kind of pop-culture collision Victoria’s Secret has been chasing in its newer era. The runway included surprise appearances from major names including Gisele Bündchen, alongside returning favorites such as Alessandra Ambrosio and Adriana Lima. Bella Hadid opened the show, while the wider event leaned into the old-school Angel spectacle with a modern celebrity ecosystem attached.
In that lineup, Kylie was not just another famous person in a famous outfit. She was the surprise package — the person whose name was held back until the runway lights were already on.
And yes, Timothée was watching
Chalamet’s presence gave the moment its inevitable social-media subplot. Page Six reported that he was seated beside Kris Jenner and Corey Gamble as Kylie made her debut, placing the actor directly inside one of the most photographed family audiences imaginable.
The relationship has already made the pair a favorite subject of the internet’s celebrity analysis department, and a front-row appearance at a $50 million Fantasy Bra reveal is unlikely to reduce the attention. It is a particularly glossy kind of couple sighting: no dramatic red-carpet pose required, just Timothée in the audience while Kylie turns a runway into a family viewing party.
Neither the setting nor the styling suggested a low-key night. Kylie’s look was designed to be seen from the back row, the cheap seats and every phone held above the crowd. Timothée’s place beside Kris only sharpened the sense that this was not simply a modeling booking; it was a major Kylie Jenner event, complete with boyfriend cameos and momager proximity.
The Fantasy Bra has previously been worn by Victoria’s Secret royalty including Gisele Bündchen, Heidi Klum and Adriana Lima. Claudia Schiffer introduced the “Million Dollar Miracle Bra” in a 1996 ad campaign, while Klum became the first model to wear a bejeweled bra on the televised runway in 2001. Bündchen’s $15 million “Red Hot Fantasy Bra” held the record for the most expensive version until this year.
Now Kylie has entered that very sparkly lineage without spending years as an Angel first. She skipped the slow build and went straight to the diamond-clad headline.
Some runway debuts ask the audience to remember a new face. Kylie’s asked everyone to remember the number: $50 million, four thousand-plus diamonds, one very familiar family, and a boyfriend watching from the dark as she made the whole thing look almost effortless.
Jason Sudeikis Finally Names the Thing He’d Change About Olivia Wilde Split
Five years after their nine-year relationship ended, the Ted Lasso star says the lesson was painfully simple: stop expecting people to read your mind.
Jason Sudeikis has offered the rarest kind of breakup postmortem: one that does not require a subtweet, a revenge dress or a suspiciously timed vacation photo. His big lesson from the end of his nine-year relationship with Olivia Wilde? He should have communicated better.
That may sound almost aggressively reasonable for a celebrity breakup that has lived in the public imagination for years, but there is something striking about hearing Sudeikis say it out loud. During Sunday’s episode of Talk Easy with Sam Fragoso, the Ted Lasso star was asked what he would have done differently in the relationship. His answer was immediate and blunt: “I think it’s just flat-out communication.”
Then he made it more personal. “I could have communicated better with how I felt, how things were making me feel [and] how things make me feel,” Sudeikis said. Translation: feelings do not become less real because you leave them sitting in the drafts.
The breakup lesson is painfully unglamorous
Sudeikis, 51, went on to explain that keeping quiet does not make an uncomfortable feeling disappear. It simply turns the feeling into a future problem, preferably one that arrives at the worst possible moment and with a much larger invoice.
“If I’m feeling a certain way and I don’t talk about it, that doesn’t make it go away,” he said. He also called it “unfair” to assume another person should be able to read your mind, whether that person is a partner, a boss at Saturday Night Live or a line producer on a television show.
That widening of the lesson is very Sudeikis: take the intimate relationship autopsy and turn it into a workplace seminar. But it also makes his point more interesting. He was not presenting communication as a magic trick that would have saved the relationship. He was talking about a habit he wishes he had developed sooner — saying what was happening internally before everyone else had to guess.
“How do you convey those ideas quicker?” he asked. It is less a grand romantic revelation than a brutally practical one. The kind of sentence people say after years of realizing that “I’m fine” is not a communication strategy.
Five years later, the emotional math has changed
Sudeikis and Wilde began dating in 2011 after meeting at a Saturday Night Live party. They became engaged in 2013 and welcomed two children: son Otis Alexander in 2014 and daughter Daisy Josephine in 2016. They parted ways in 2020 after nearly a decade together.
In the interview, Sudeikis was asked whether he understands the breakup differently now than he did at the time. His answer came wrapped in a very specific piece of heartbreak arithmetic: the idea that getting over something takes half as long as the relationship itself. For a 10-year relationship, he said, five years would be “20/20.”
It is an extremely dad-joke-adjacent way to describe emotional distance, but the timing is notable. The relationship ended in 2020, meaning Sudeikis is now speaking from roughly the point he described — far enough away to see the shape of what happened, but not so far away that the experience has become irrelevant.
That is the difference between a fresh breakup statement and a later reflection. In the early aftermath, everyone wants a villain, a timeline and a single moment when the romance supposedly went off the rails. Years later, the story can become less cinematic and more recognizable: two people who shared a life, failed to say some things clearly enough, and had to learn how to remain connected as parents after no longer being partners.
He is not dragging Wilde — which is almost the twist
Sudeikis did not use the conversation to take a swipe at Wilde, who directed Don’t Worry Darling and has continued working in film. Instead, he spoke warmly about her career and said he was “thrilled for her.” He also called her “very good” at her job.
That praise matters because celebrity exes are often expected to perform one of two roles: the wounded innocent or the enlightened best friend. Sudeikis lands somewhere less satisfying and more human. He acknowledges his own shortcomings without turning the relationship into a self-help brand, and he speaks positively about Wilde without pretending the split was a cute little chapter everyone giggled through.
“I feel very fortunate doing what I’m supposed to be doing,” he said. “But going through all that has allowed me to see when other folks are going through something similar.”
There is a quiet shift in that sentence. The relationship is no longer just something that happened to him. It has become a lens he uses to recognize pain in other people. That is not exactly an apology, and it is not a reunion announcement. It is the more complicated middle ground celebrities rarely offer because it does not fit neatly into a headline.
The public has had plenty to track since the split. Sudeikis was romantically linked to Keeley Hazell from 2021 to 2022. Wilde dated Harry Styles from 2021 to 2022 and was later linked to actor and former basketball player Dane DiLiegro in 2025. She has since moved on with Casper Jopling, according to Page Six.
But Sudeikis’ interview is not really about who came next. It is about what remains after the glamorous part of a breakup has burned off: co-parenting, professional respect, old patterns and the uncomfortable realization that silence is not the same thing as peace.
For all the chaos that tends to surround famous former couples, his conclusion is almost offensively sensible. Say what you feel. Say it sooner. Do not assume the person beside you has a psychic subscription. And if you fail at that, at least have the humility to learn the lesson without making your ex carry the entire story.
Conor Kennedy’s Rio Wedding Had Christ the Redeemer, Samba Dancers and One Very Carolyn Bessette Dress
The Kennedy heir and Brazilian pop star Giulia Be turned their already-legal marriage into a three-day Rio love letter — complete with beach volleyball, historic churches and a football check-in.
Conor Kennedy and Brazilian pop star Giulia Be were already married on paper. Rio de Janeiro, apparently, was where they wanted the full cinematic universe.
The couple celebrated their wedding with a three-day party across the city earlier this month, trading the usual banquet-hall choreography for Christ the Redeemer, Ipanema beach volleyball, samba dancers and a historic mansion in Jardim Botânico. It was part wedding, part destination vacation, part extremely well-cast travel editorial — and, naturally, the Kennedy family brought the cameras along.
Kennedy and Giulia Be, whose full name is Giulia Bourguignon Marinho, reportedly held a private civil ceremony in Los Angeles in March, according to Vogue. The Rio festivities, which began Oct. 8, were the larger celebration: a way for the Brazilian singer to bring Kennedy’s family and friends into her world while giving the family’s famously mythologized name a tropical new backdrop.
She said no to Massachusetts
Marinho had a very clear vision for the wedding location. Earlier this year, she told Brazilian outlet Globo that Rio was “the only chance to bring all of [Kennedy’s] friends and all of his family to Brazil” and that she wanted to show them a good time.
Her position on the alternative was even more direct. “My love, I love you, but I’m not getting married in Massachusetts,” she recalled telling her then-fiancé.
Honestly, the woman understood the assignment. Massachusetts might offer Kennedy family history, old-money architecture and enough autumn foliage to power a prestige miniseries. Rio offered beaches, mountains, historic streets and the kind of skyline that does not require a filter. The couple’s three-day itinerary made the choice look less like a rejection of tradition than an upgrade to something deeply personal to the bride.
The festivities reportedly opened with a welcome party in the hills of Alto da Boa Vista. Guests then played beach volleyball on Ipanema before heading up Corcovado Mountain for a blessing beneath the Christ the Redeemer statue. That is not a casual wedding stop. It is a location with built-in grandeur, sweeping city views and the unmistakable energy of a couple determined to make their family album look like a tourism campaign.
Marinho told Vogue, “We wanted to celebrate not just the wedding, but also Rio de Janeiro, the city we love.” She described being at Christ the Redeemer with their family as a moment she would never forget.
The dress had a Kennedy echo
For the blessing, Marinho wore a Calvin Klein slip dress that Vogue noted evoked the understated elegance of Carolyn Bessette Kennedy, the late wife of Conor’s uncle John F. Kennedy Jr. It was a pointed but graceful style reference: not a costume, not a logo parade, just the clean lines and low-volume glamour associated with one of the most scrutinized fashion figures in the Kennedy orbit.
The choice gave the wedding a little extra visual intrigue. Giulia Be is a pop star with her own public identity and a Brazilian home base; the slip dress nodded toward Kennedy mythology without swallowing her inside it. The effect was less “trying to become a Kennedy” than “knowing exactly which chapter of the family’s visual history photographs best.”
The ceremony itself took place at Igreja Nossa Senhora do Carmo da Antiga Sé, a church in Rio’s historic center. The building dates back to 1808, when the Portuguese royal court arrived in Brazil, and it served as a royal chapel and cathedral. The setting supplied the old-world drama, while the surrounding area offered the city’s more lived-in texture: historic squares, waterfront views and the nearby Praça XV de Novembro flea market.
Then came the reception at Instituto Brando Barbosa in Jardim Botânico, a neighborhood known for the Rio de Janeiro Botanical Garden and its lush historic grounds. If the couple wanted a single aesthetic to summarize the weekend, it was apparently “royal chapel meets tropical garden party,” with a little celebrity-family spectacle folded in.
Even the family photos had a plot
Robert F. Kennedy Jr. shared photos from the celebrations on social media, giving the public a glimpse at the family’s Rio takeover. The images included the wedding party beneath Christ the Redeemer, Cheryl Hines dancing with a Brazilian dancer and the newly married couple checking their phones for updates on the Seminoles-Cardinals game.
That last detail is particularly charming because it punctures the polished destination-wedding fantasy at exactly the right moment. Yes, there was a monumental statue, a historic church and a glamorous pop star in a Calvin Klein slip dress. But there was also a sports score to monitor. Even the most photogenic wedding weekend has somebody asking what happened in the fourth quarter.
Hines, Kennedy’s wife, appeared in the family images alongside former NASCAR driver Danica Patrick, while the Rio festivities made room for both Kennedy-family familiarity and Brazilian celebration. The bride commented on one of the Instagram posts, “Love you, Bobby,” and added that it made her happy to see everyone enjoying her hometown.
That warmth is the real through line here. This was not just a wedding imported into an exotic location for the sake of scenery. The scenery was the point. Marinho wanted Kennedy’s relatives and friends to experience the city as she knows it, and the celebration moved accordingly: from the hills to the beach, from the mountain to the church, from the historic center to the botanical district.
Conor Kennedy, a grandson of the late Sen. Robert F. Kennedy and a son of Robert F. Kennedy Jr., arrived with one of the most recognizable surnames in American public life. Giulia Be brought a Brazilian pop-star sensibility and a hometown big enough to hold the occasion. Together, they produced a wedding that managed to be grand without feeling trapped in Kennedy formalwear — a family event with a Rio pulse.
And somewhere between the samba dancers, the Christ the Redeemer blessing and the football updates, the couple found the sweet spot: glamorous enough for the family archive, relaxed enough to feel like an actual party, and stylish enough to make Massachusetts seem like a nonstarter.