The recent Santa Barbara International Film Festival provided a mesmerizing backdrop for the celebrity couple Kylie Jenner and Timothée Chalamet. As stars of the evening, they turned heads with their striking appearances and undeniable chemistry. Dressed to impress, Jenner, a seasoned entrepreneur and social media influencer, donned a stunning vintage Azzedine Alaïa black dress from the designer’s 1998 spring collection. This embossed garment, which accentuated her figure, served not just as a fashionable statement but also as a historical nod, given that it was released in the very year she entered the world. Adding a sense of exclusivity to her ensemble, the dress carries an astonishing price tag of $30,000 on a luxury resale platform, 1stdibs.
Jenner’s flair for fashion was further complemented by dazzling jewelry pieces provided by the esteemed Lorraine Schwartz. She adorned her fingers with two exquisite diamond rings—one emerald-cut sparkler on her pointer finger, picture-perfect for capturing the light, and an elegant oval diamond perched on her pinky. The allure didn’t stop there; she completed her look with striking diamond studs and coordinating silver earrings that effortlessly enhanced her vintage style. This penchant for vintage Alaïa dresses indicates Jenner’s fashion philosophy—favoring timeless pieces that resonate with her identity while making bold statements on red carpets.
Timothée Chalamet, a formidable figure in the film industry, also showcased his style, albeit with a more playful approach. Sporting a vibrantly colored floral button-down shirt from Prada, adorned in shades of green and yellow, he layered it over a lime green tank top. His bottom half featured casually stylish baggy True Religion bootcut jeans, and he completed the ensemble with chic white Bape sneakers. Not one to shy away from accessories, Chalamet also wore a diamond choker necklace, adding a touch of sophistication to his look. His bold choices evince a youthful spirit and a desire to stand out, a significant aspect of Chalamet’s fashion identity.
While they are known for being private about their relationship, Jenner and Chalamet’s mutual support was palpable during the festival. Observations captured by attendees revealed Jenner affectionately rubbing her boyfriend’s back prior to him receiving the Arlington Artist of the Year Award for his remarkable performance in “A Complete Unknown.” This moment not only illuminated their closeness but also showcased how their romantic bond complements their respective careers in the spotlight.
Having first sparked rumors of their romance in April 2023, the pair has made several public appearances together, albeit sporadically. Their attendance at the Golden Globes 2025 was one such occasion, highlighting Jenner in a stunning vintage Versace dress, and the couple’s subsequent rendezvous at an afterparty following Chalamet’s hosting stint on SNL further highlighted their dynamic. These instances reveal a willingness to occasionally share their love story with the world despite a generally enigmatic approach to their personal life.
As anticipation builds around future glamorous events, one cannot help but wonder what fashion statement Jenner will unveil next, especially with the Oscars just around the corner. With a shared affinity for high fashion and a penchant for dramatic appearances, it is likely that Jenner, once again, will embrace her inner fashionista, delivering an iconic look while making headlines alongside Chalamet. This couple continues to be a focal point of media attention—not for mere appearances but as influencers of style and modern romance, capturing the hearts of audiences everywhere.