17-year-old model Kai Schreiber joined her mother Naomi Watts and a star-studded guest list at designer Michael Kors' 45th anniversary celebration dinner in East Hampton, New York, on Thursday night. The high-profile event brought together leading figures from film and fashion to mark four and a half decades of the iconic American brand.
Schreiber, the daughter of Watts and actor Liev Schreiber who walked the runway at Paris Fashion Week, made a striking appearance in a chic black dress-over-pants ensemble as she mingled with celebrities including Katie Holmes, Carolyn Murphy, and Christie Brinkley.
Star-studded gathering in East Hampton
The high-profile dinner was held in East Hampton, a seaside resort town on the South Fork of Long Island known as a summer retreat for high society and entertainment figures. Guests gathered to honor Kors, 67, whose upcoming Fall/Winter 2026 collection focuses on urban simplicity and luxury. The collection highlights soft layering with a color palette spanning from city neutrals to vibrant hues.
Supermodel Christie Brinkley, renowned for her legendary career including record-breaking appearances on the cover of the Sports Illustrated Swimsuit Issue, arrived with her daughter Sailor Brinkley. Both mother and daughter wore elegant red outfits, with Brinkley resplendent in a coordinated top-and-pant set while her lookalike daughter opted for a red dress.
High fashion styling on the red carpet
Kai accessorized her fashion-forward outfit with a chic black purse and black, block-heeled sandals featuring square toes. Her hair was styled in an elegant knot with side-sweeping bangs as she posed for photographs alongside her mother and Kors.
Watts, the 57-year-old Academy Award-nominated actress known for her acclaimed performances in films such as Mulholland Drive and The Impossible, displayed modern charm in a white blouse with an asymmetrical neckline paired with tapering black slacks featuring side pockets. Watts lent Kai her unwavering support throughout the celebrity-friendly bash.
Actress Katie Holmes, 47, famous for her television role in Dawson's Creek and films including Batman Begins, also attended the celebration. Holmes looked pretty in a softly flowing purple dress accessorized with red, square-toed heels and a white purse. She was joined at the event by her new artist boyfriend, 38-year-old Jason Bard Yarmosky.
During the festivities, Watts and Holmes posed together with host and man of honor Michael Kors, who founded his eponymous luxury fashion house in 1981.
Ambitions on the runway
Kai has long harbored aspirations of building a career on the fashion runway. Speaking to Interview magazine last year, the young fashionista revealed that her modeling ambitions were closely tied to her personal journey with gender identity and her desire to be a beautiful, glamorous woman.
"I want to be a supermodel. Period. I've been practicing my walks in the kitchen for years. My mom can show you all the videos I forced her to film," Kai told the publication. She added: "Struggling with gender identity from a young age most likely had something to do with it. I always wanted to grow up and be a beautiful, glamorous, influential woman, like Marilyn [Monroe]."
Kai made her official runway debut for luxury fashion house Valentino in March 2025. Since stepping onto the catwalk, she has modeled for several major fashion houses, including Mugler, Jason Wu, Fendi, Celine, and Jean-Paul Gaultier.
Transgender representation in high fashion
In her interview, Kai expressed deep gratitude for the supportive community of transgender models working within the fashion industry today.
"As a young trans girl, I'm always going to look up to the older generation of transgender people, especially in fashion," Kai explained. She cited prominent trans figures as inspirations: "People like Alex Consani, Hunter Schafer, Hari Nef, Dara, Richie Shazam, Colin Jones, and so many more."
Reflecting on the importance of solidarity, Kai noted: "It's so great that there's a strong community of us in the fashion world; it's really a doll takeover. It's important to all of us to have a sense of community, especially when we're under such hostile attack."
At the time of the interview, the teenager reflected on her future plans and whether she intended to pursue higher education or focus entirely on her modeling career.
Asked about her educational aspirations, Kai stated: "I don’t know. Like I said, school has never really been my strong suit." She expanded on her career focus, adding: "I see myself in the fashion industry. It's always been my dream. I'm not sure if college is for me, but we'll see when it rolls around. I like to go with the flow."
Support from father Liev Schreiber
Kai's father, 58-year-old actor Liev Schreiber, best known for playing the title role in the acclaimed television drama series Ray Donovan, spoke candidly last year about supporting his child. In an interview with Variety senior culture editor Marc Malkin, Schreiber recalled sharing a profound moment with his child when she asked her family to begin using feminine pronouns.
"Kai was always who Kai is," the actor said of his child. "But I suppose the most profound moment was her asking us to change her pronouns. To be honest with you, it didn't feel like that big of a deal to me only because Kai had been so feminine for so long."
The actor praised his daughter's courage and openness, stating: "Kai is such a fighter. It's important that she goes, 'Hey, I am trans,' and, 'Look at me.'"
Family history and new chapters
Watts and Schreiber were together for eight years after meeting at the Met Gala in the spring of 2005. Although the couple never married, they raised two children together, Kai and her older sibling Sasha, 19, before announcing their separation in September 2016.
Both parents have since remarried and built new family lives. Watts wed actor Billy Crudup in June 2023 during a low-key ceremony at a Manhattan courthouse. Meanwhile, Liev Schreiber exchanged vows with former pageant queen Taylor Niesen in July 2023, and the couple welcomed their first child together, Hazel Bee, one month later.
