Kylie Jenner undeniably turned heads at the Santa Barbara International Film Festival, where she stepped out to support her partner, Timothée Chalamet, on Tuesday night. The 27-year-old entrepreneur stunned in a sleek, vintage black halter dress that exuded timeless glamour. The gown, sourced from Azzedine Alaïa’s spring 1998 collection, held special significance, as it debuted the same year Jenner was born. Styled by Mackenzie Grandquist and Alexandra Rose, the look was nothing short of breathtaking. The curve-hugging, low-back design not only showcased Jenner’s enviable figure but also carried a hefty price tag of $30,000, as listed on luxury resale site 1stdibs. The choice of such a rare and iconic piece underscored Jenner’s commitment to making a fashion statement, proving once again why she’s a household name in the beauty and style world.
Jenner’s overall ensemble was elevated by her impeccable jewelry choices. She accessorized with two show-stopping diamond rings from renowned jeweler Lorraine Schwartz. A radiant emerald-cut sparkler adorned her pointer finger, while an oval diamond graced her pinky. Adding to the dazzle were statement diamond studs and coordinating silver earrings, which completed her sophisticated yet glamorous look. The combination of vintage haute couture and modern, high-end jewelry highlighted Jenner’s ability to seamlessly blend eras and styles, cementing her status as a fashion icon. Her choices for the night were undeniably bold yet understated, making her one of the standout attendees at the event.
Interestingly, this isn’t the first time Jenner has turned to Alaïa’s iconic designs for a high-profile outing. Just last month, during Paris Haute Couture Week, she donned a see-through leopard minidress from the designer’s 1991 collection. This recent affinity for vintage Alaïa pieces may have been inspired by her older sister, Kim Kardashian, who famously wore a leopard catsuit by the same designer back in 2019. It seems the Jenner-Kardashian siblings continue to influence each other’s fashion choices, creating a ripple effect in the style world that fans and critics alike can’t help but notice. Jenner’s decision to revisit Alaïa’s archives speaks volumes about her appreciation for timeless designs and her confidence in pulling off looks that are both daring and elegant.
Meanwhile, Timothée Chalamet, Jenner’s beau,Also made a bold fashion statement at the event, though his outfit took on a decidedly different vibe. The actor, who was honored with the Arlington Artist of the Year Award for his performance in A Complete Unknown, opted for a vibrant Prada floral button-down shirt in shades of green and yellow. Layered over a lime green tank top, the look was both eye-catching and modern. Chalamet paired the ensemble with baggy True Religion bootcut jeans and crisp white Bape sneakers, adding a diamond choker necklace for an extra touch of glamour. While his outfit was undeniably less traditional than Jenner’s, it showcased his willingness to embrace bold colors and patterns, proving his fearless approach to fashion.
As usual, Chalamet walked the red carpet solo before meeting up with Jenner inside the venue. A heartwarming video captured the moment Jenner affectionately rubbed his back as he prepared to accept his award, offering a rare glimpse into their private relationship. Though the couple has kept their romance relatively under wraps since being first linked in April 2023, they’ve made a few notable public appearances together. One of their most memorable outings was at the Golden Globes 2025, where Jenner dazzled in a vintage Versace dress with a daringly low back. Subtle yet supportive, their interactions suggest a deep connection, even as they maintain their independence in the public eye.
Looking ahead, all eyes are on what Jenner will wear next, particularly with the Oscars just around the corner. Her ability to command attention with her sartorial choices is unmatched, and her recent affinity for vintage Alaïa suggests she’s poised to make even more memorable appearances. As for Chalamet, his bold fashion choices continue to solidify his status as a style icon in Hollywood. Together, the couple’s commitment to taking risks in their wardrobes makes them a compelling duo to watch, both on and off the red carpet. Whether they’re stepping out for high-profile events or keeping a low profile, Kylie Jenner and Timothée Chalamet undeniably bring their own unique brand of glamour to every occasion.
