Supermodels and best friends Kendall Jenner and Hailey Bieber consistently captivate on the red carpet, especially at the prestigious Academy Museum Galas. Their joint appearances, marked by contrasting yet equally stunning fashion choices, highlight a dynamic friendship spanning over a decade, offering fans a glimpse into their enduring bond amidst the dazzling world of Hollywood.
The worlds of fashion and film converged once again at the illustrious Academy Museum Gala, where Kendall Jenner and Hailey Bieber made joint appearances that underscored not only their individual style prowess but also their celebrated long-standing friendship. These red carpet moments have become a testament to their unwavering bond, showcasing how these “it girls” navigate fame together, often with sartorial statements that complement their unique personalities.
A Decade of Dynamic Duo: The Foundation of Their Bond
Kendall Jenner and Hailey Bieber‘s friendship traces back to 2012, a bond that began through Kylie Jenner. Hailey reminisced about their first encounter at “The Hunger Games” premiere during an episode of her YouTube series “Who’s in My Bathroom?”. Over the years, their connection deepened as they navigated the demanding worlds of modeling and entertainment together, evolving into what Jenner affectionately describes as “sisters.”
Their journey has been marked by shared milestones, from walking runways together for designers like Sherri Hill in 2014 to celebrating personal events like Hailey’s 18th birthday and Kendall’s 21st. They even cemented their friendship with matching tiny broken heart tattoos in August 2015. This enduring partnership has seen them support each other through professional endeavors and personal growth, a rare feat in the fast-paced industry they inhabit. Hailey has praised Kendall’s loyalty, noting, “when Kendall loves, she loves super hard.” More insights into their relationship were shared during Bieber’s Who’s In My Bathroom YouTube series, where they reflected on their mutual support and understanding as reported by Elle.
Gala Glamour: A Look Back at Their Academy Museum Moments
The Academy Museum Gala, a significant event celebrating the movie industry, has twice served as a platform for Kendall and Hailey to showcase their unique fashion sensibilities side-by-side.
2023: Contrasting Hues and Signature Styles
At the 2023 Academy Museum Gala, held in December, the best friends opted for strikingly different, yet equally impactful, floor-length gowns. Kendall Jenner exuded sophistication in a vibrant red long-sleeved turtleneck gown from Fendi’s Fall/Winter 2023 couture collection. The piece featured a bandage-like bodice that cinched her waist, worn without a bra, and styled simply with strappy red sandals and small silver hoop earrings. Her makeup was glowy with a glossy pink lip, and her hair flowed in a messy, straight ‘do.
In contrast, Hailey Bieber brought a red carpet twist to her signature sleek look, choosing a black sequin halter neck gown by Saint Laurent. She complemented her dress with black sandals, large diamond drop earrings, glazed-doughnut glowy makeup, a subtle cat eye, painted-on freckles, and a black manicure. Her hair was pulled back into a neat ballerina bun. Their contrasting choices perfectly embodied their personal styles, creating a memorable fashion moment at the event, which also honored figures like Meryl Streep and Oprah Winfrey as covered by Harper’s Bazaar.
2025: Sophistication and Architectural Elegance
The duo returned to the Academy Museum Gala on October 19, 2025, for its 5th annual iteration, once again posing together in distinctly different ensembles. Jenner embraced minimalist sophistication in a sleeveless black dress from The Row. The gown elegantly followed her figure before flaring out slightly, paired with black sandal heels.
Bieber, meanwhile, made a bold statement in a chocolate and tan couture gown from Schiaparelli’s Spring 2025 collection. Her dress featured a corseted bodice and a thigh-high slit, accented by a striking silver floral brooch. These looks further solidified their reputation for bringing individual flair to collective appearances.
Beyond the Red Carpet: A Friendship Forged in Fame
Their joint appearances extend far beyond the Academy Museum Gala. In April 2025, their respective brands, Jenner’s 818 Tequila and Bieber’s rhode, collaborated for a Coachella photo booth activation, playfully dubbed a “bestied so hard our brands collabed.” They are frequent fixtures at high-profile events, including multiple Met Galas, where they often arrive in complementary, yet individualistic, styles.
For instance, at the 2025 Met Gala, themed “Superfine: Tailoring Black Style,” they walked hand-in-hand. Bieber sported a Saint Laurent by Anthony Vaccarello blazer mini dress with Tiffany & Co. jewelry, while Jenner opted for a custom gray skirt suit by British designer Torishéju, adorned with Chopard diamond jewelry.
Just the night before the 2025 Academy Museum Gala, they were seen celebrating at the King Kylie pop-up event for Kylie Cosmetics. Kendall donned a vintage blue suede Calvin Klein dress, while Hailey chose a long black Saint Laurent dress, once again highlighting their dynamic fashion choices even at more casual, pre-gala gatherings.
A Style Legacy: What Their Joint Appearances Mean for Fans
For fans, the joint appearances of Kendall Jenner and Hailey Bieber are more than just fashion showcases; they are a celebration of a friendship that has weathered the unique pressures of celebrity. Their ability to maintain a supportive and genuine connection, visible in their easy camaraderie on red carpets and in social media posts, resonates deeply with their audience.
Whether they’re called “sisters” or likened to a “golden retriever and black cat” duo, their contrasting styles and complementary personalities provide endless fascination. These moments reinforce that even amidst the glamour and scrutiny of Hollywood, authentic bonds can thrive, offering a relatable narrative of companionship and shared experiences that fans cherish.
