She doesn’t want to be known as a “nepo baby” and would probably shudder at the thought of being called a “Gen Z socialite.” But model-content creator Sailor Brinkley Cook is an influencer — and she hopes to be a positive one. “I like to think of myself as mayor of the Hamptons,” she tells Alexa. “I am the biggest advocate [for the area]. Due to summer crowds, it can get a certain reputation, but the people who were born and raised in the Hamptons are some of the best people I’ve met in my life.” 

Brinkley Cook, who grew up on Bridgehampton’s Tower Hill estate (the site of our cover shoot), comes off as much more salt of the earth than celebutante, and that’s likely because of her incredibly close and supportive blended family — including model mom Christie Brinkley, real estate agent-architect dad Peter H. Cook, older sister Alexa Ray Joel (whose dad is Piano Man Billy Joel) and big brother Jack. 

Rather than retreat from the inevitable comparisons that come with having a supermodel (and former Alexa cover star) mom, Brinkley Cook leans into them with a wink and a smile. “Growing up with Christie Brinkley as a mom, it’s like the [Fountains of Wayne] song ‘Stacy’s Mom,’” she laughs, breaking into her own rendition: “‘Sailor’s mom has got it going on.’” It’s a narrative the 27-year-old has lived with her whole life — and she’s not only learned to love it, but finds her mom aspirational. “I’m like, ‘Rock on!’ I hope to be a MILF one day, too.”

She and her look-alike mom, 72, often co-star in videos on TikTok and Instagram (from periodic ’fit checks to comedically dropping f-bombs while rapping along to Megan Thee Stallion). “We have a really fun dynamic,” shares Brinkley Cook. “She’s a Disney princess and I’m the little troll under the bridge being like, ‘Do something funny!’” 

Brinkley Cook’s relationship with her dad, 66, is less public, but just as solid (he and Brinkley divorced in 2008). She calls him her “rock” and says she “adores him.” She’s equally enamored of her siblings, Jack, 30, and Alexa, 40. “[Other than my parents], these are the only two people that have known me my entire life — [they know] my whole past and will know my entire future. I’m extremely grateful we’ve always been super tight-knit.”

Inarguably, Brinkley Cook was born into a life of privilege, and she understands that some doors have opened because of her pedigree. But the Parsons School of Design-trained photographer insists it’s her work ethic and persistence that keep them open. She never set out to follow in her mom’s footsteps, but when you’re the daughter of one of the world’s top models and are a tall beauty yourself (now 5-foot-10), agencies come to you. 

At 15, while attending the Ross School in East Hampton, she signed with IMG Models. A campaign for Claire’s and editorials for Teen Vogue and Seventeen soon followed. Then, the Sports Illustrated Swimsuit issue came calling; in her debut issue, the head-turner posed with her mom and sister before returning as a solo Rookie in 2018. Eventually, she was walking runways for Dolce & Gabbana in Milan and Elie Tahari in NYC.

But Brinkley Cook says her interest in modeling was overshadowed by incessant imposter syndrome. “I wanted to be a part of this world, but there was just something innate in me that felt like my body, my face — and my everything! — just wasn’t good enough, and I didn’t deserve to have these opportunities because I’m not Gisele Bündchen or Christie Brinkley.” Those self-doubts led to a yearslong struggle with disordered eating and body dysmorphia.

“I have been in the public eye since I was a newborn,” she explains. “And I have heard comments like, ‘Oh, she’s so ugly.’ ‘She’ll never be Christie Brinkley.’ ‘Her body is gross.’ ‘She’s just a plain Jane.’ I will always have that little demon inside of me saying, ‘You’re not enough.’” But with years of therapy under her belt, she’s found a way to work through it. “It’s a matter of killing the demon — every single day,” she tells Alexa. “Because nothing good comes out of hating yourself.”

Her hearthstone and safe place remains Tower Hill. The house and guesthouse, which have a combined 10 bedrooms and 13 baths, share the 20-plus acres with a greenhouse, chicken coop, barn turned art studio and pool. It was purchased and renovated in 1998, the same year she was born. 

“It’s the only house I’ve ever lived in,” says Brinkley Cook. (A Manhattan apartment is now her official home, but she takes the Jitney or drives her VW Bug back to Bridgehampton every chance she gets.) “It’s the most amazing hodgepodge of art and furniture from all of the places around the world that my mom’s traveled, that we’ve traveled. So, everything in the house has a story to it, which is really special. People love minimalism and that’s all good. I’m not trying to yuck anyone’s yum, but I love maximalism — in a home, especially.”

Tower Hill’s yard — which is often visited by wild deer, rabbits, foxes and turkeys — is her favorite place to be with her cavapoo, Lion (short for Lionel). Inside, the family gathers and often makes pasta and caprese salad together. This summer, they’re going to try to animal-proof their garden, so they can keep some of their bounty of tomatoes, kale and snap peas for themselves. 

The Hamptons native has her favorite local spots, like nearby Provisions, where she ordered in a house salad with tempeh and avocado during our shoot; Carissa’s in Sag Harbor for its Brussels sprouts sandwich; and Surf Lodge in Montauk for late-night dancing. She loves the harvest festival in the fall and driving the family Jeep through the snow on the beach in winter.

After a break from being in front of the cameras, she recently signed with Ford Models and also works as a content creator for BrainJuice liquid supplements. “I feel like a caterpillar growing into a butterfly,” she reflects. “I can’t wait for new creative experiences.”

She traces her growing confidence back to a moment in 2019 when her mom broke her arm and Brinkley Cook was asked to step in and replace her on Season 28 of “Dancing With the Stars.” 

“That was the coolest experience of my life,” she says, before adding that she initially turned it down. “When my mom proposed it, I said, ‘Absolutely not. That’s not happening!’” 

The self-professed overthinker had convinced herself she’d never be a performer after a bout of crippling stage fright at age 7 forced her to pull out of her role as Christopher Robin in Sag Harbor’s Bay Street Theater production of “Winnie the Pooh.” “So it was really cool to experience that shift of being like, ‘I can’t do this … Oh, wait, I can.’ It changed the trajectory of my life.

“The lesson that came out of that experience was to always be open to trying, even if I fail. And I did fail, and very publicly. I sobbed on national television with a snot rocket dripping down my face.” 

(Brinkley Cook has embraced that moment in all its whimpering glory. Every season premiere of “DWTS,” she posts the image on Instagram for laughs.) Her only regret? Being voted off the show before controversial former White House press secretary Sean Spicer. 

Still, she had an impressive run for a last-minute sub, making it through six episodes and competing in the foxtrot, rumba, tango, cha-cha-cha, Viennese waltz and jive (that last dance was the one that got her eliminated, despite receiving nines from three judges).

Now, after six years of steady affirm-ations, Brinkley Cook is welcoming her “Year of Yes,” and vowing not to say no to things that scare her. “As a Cancer, I love being cozy in my comfort zone,” she explains. “And I have really been trying to push myself, because I think that life starts at the end of your comfort zone. That’s when the things I’m gonna tell my [future] kids about are going to happen.” 

She’s determined not to let any outside pressures to be perfect kill her dreams. “Being a celebrity’s child, everyone’s like, ‘All right, so where’s your brand? Your clothing line?’” explains Brinkley Cook. “You’re expected to have it all figured out by the second that you get your period.”

Instead, she prefers to think of herself as an ever-evolving work in progress. This summer, the nature lover is taking a leadership role in Project Zero’s the Coral Collective beach cleanup in
Sagaponack on June 7, along with a benefit dinner and silent auction in August. The pescatarian’s love for the ocean comes from her family time in the Hamptons and their vacation home in Turks and Caicos, where she’s seen the change in the reefs firsthand.

The licensed health coach (certified through the Institute for Integrated Nutrition) also hopes to one day create a hormonal supplement brand for women to help with things like premenstrual dysphoric disorder (a condition she’s been diagnosed with and which she describes as “heightened PMS”). 

“The idea of being able to create something in my life that helps people is the goal,” says Brinkley Cook. “I don’t know exactly how I’ll do that yet, but I am very passionate about wanting people to feel good.”

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Photographer: Eduardo Rezende; Editor: Alev Aktar; Stylist: Anahita Moussavian; Photo Editor: Jessica Hober; Talent Booker: Patty Adams Martinez; Hair: David Cotteblanche; Makeup: Chichi Saito For Art Department Using Charlotte Tilbury; Digital Tech: Niccola Civita; Photo Assistant: Annette Milburn; Fashion Assistant: Dominic Turiczek; On-Set Assistants: Yared Glicksman, Nick Parisse; Contributing Editor: Serena French