Other nights, however, Hollywood doesn’t require a premiere to refurnish the town but merely a gala. The 2025 Academy Museum Gala demonstrated as much with its blue carpet so heavy with couture and star power, it might have illuminated Wilshire Boulevard for a week.
This fifth gala fundraiser wasn’t just about raising over $12 million for the museum’s exhibitions and education programs but that was part of it for certain. It was an evening of art, heritage, and style. Honorees Bruce Springsteen, Penélope Cruz, Bowen Yang, and Walter Salles provided the evening’s gravitas, and fashion brought sheer fantasy.
From ancient rocks to straight-off-the-catwalk slogans, the evening’s fashion spoke volumes about heritage, imagination, and innovation. Here are the top ten most symbolic fashion moments of an evening when Hollywood’s crème de la crème gazed upwards as if the museum’s next blockbusters.
1. Kim Kardashian’s Masked Maison Margiela Moment
Kim Kardashian closed off the blue carpet in a similarly impossible-to-recognize and haute-fashion look. She was the final one to come out, sporting a blank face mask under a strapless corseted dress in the same color from Maison Margiela Fall 2025 Couture. The look was so futuristic and sculptural that she required help manning doors. It was an energy-overload move that was one step removed from performance art and red carpet diva, and placed her in the mix with one of the night’s most discussed guests.
2. Jenna Ortega’s Futuristic Grace Ling Couture
Jenna Ortega rocked the gothic glamour aesthetic in one of the ensembles from Grace Ling’s spring 2026 collection the “leaf petal couture dress.” Her silver breastpiece flowed elegantly down her neck, falling into a chocolate brown silk skirt that hugged curves on her body. Enrique Melendez styled her cherry-cold red locks into a low pony by Cesar Deleon Ramirez, and Mélanie Inglessis kept makeup moody and gorgeous. This was the latest in a string of bold, editorial-worthy red carpet victories for Ortega.
3. Olivia Rodrigo’s Retro Armani Privé Sparkle
Olivia Rodrigo drew inspiration from previous Armani Privé collections for a beaded sequin vest and floor-length skirt from the Spring 2005 Couture collection. The ensemble, which was accessorized with a crocheted black flower pinned at the collar, was completed with Chopard jewelry for understated chic. She then changed into a silver sequin ensemble by Giorgio Armani completed with Amina Muaddi Dalida Glass Platform Mules for her second back-to-back best-dressed look at the after-party hosted by Cartier.
4. Kendall Jenner’s Effortless The Row Chic
Effortless chic belonged to Kendall Jenner in sleek The Row attire, put together by Danielle Goldberg. Her selection was a nod to the evening’s de facto trend star of runway-off-the-runway dressing, but its bareknuckle beauty missed the mark. Jenner’s ensemble proved what minimalism could accomplish, when done entirely spot on, to be just as fascinating as the most angsty haute couture.
5. Hailey Bieber’s Schiaparelli Corseted Glamour
Hailey Bieber commandeered the headlines in boned, corseted Schiaparelli Spring/Summer 2025 evening wear. Ruffled skirt and boned top unleashed a show-stopping silhouette that teamed sultry contemporaneity with haute-couture flash. Blanked out past Kendall Jenner, Bieber’s look was a masterclass on how to arrive without overwhelming the moment.
6. Zoë Kravitz’s Saint Laurent Jewel-Toned Drama
Zoë Kravitz in an Anthony Vaccarello Saint Laurent runway look, all jewel color and pussy-bow blouses that flowed. The melodrama of the look was a counterpoint to overdramatic Kravitz’s laid-back beauty styling, and the tension that was created by this vision was instant and timely. It was proof of the fact that Saint Laurent’s strength is because it balances edginess and beauty.
7. Addison Rae’s Versace Silver Spark
Addison Rae glimmered like a stone under the metallic silver Versace in the red carpet lighting. Every camera flash bounced off the mirror finish, and she was the night’s paparazzi sweetheart. She captured the evening’s youth energy in her look, and she demonstrated that high-energy glamour could be paired with more demure seasonal fashion.
8. Elle Fanning’s Whimsical Balenciaga Feathers
Elle Fanning and stylist Samantha McMillen brought whimsy to the carpet with a pink t-shirt and red feather skirt straight from the Balenciaga runway. The playful mix of casual and couture reflected Pierpaolo Piccioli’s much-discussed debut for the house, and Fanning’s ease in the look made it one of the night’s most charming style statements.
9. Joey King’s Sleek Carolina Herrera Cut-Out
Joey King in Carolina Herrera black cut-out spring 2026. The soft, sensual cut was proof of Herrera’s skill at reimagining vintage silhouettes. King’s look was proof that a human might sometimes require just one show-stopping element a strategically placed cut-out to craft a whole look.
10. Jeremy Strong’s Red Nebraska-Inspired Suit
Jeremy Strong’s bleached-blonde hair, matching coloring, and radiant red suit were a deliberate homage to Bruce Springsteen’s Nebraska record. The one-hued monochromatic-colored suit was a risk at a gala but for an evening celebrating creative heritage. Strong’s appearance was authoritative not only for color, but in that it carried with it a story behind its coiffing.
The 2025 Academy Museum Gala was more than a fund-raiser, a higher good it was demonstration that fashion may be utilized to speak.
From legendary jewels to newcomers along the catwalk, every look had something from its owner’s past and something that symbolized the cultural moments building Hollywood’s future. In a town where fashion equals money, this ball was proof of the truth that the most desired fashion is the fashion that goes hand in hand with creativity, meaning, and a dash of fearlessness.
