In The Magazine

Helloooo, Sailor!

by Karen Moline Photographed by Ben Fink Shapiro
Tuesday, May 22, 2018

It’s never easy being the child of an icon, to find your own way out from the flash of the paparazzi cameras or the ceaseless judgments of snarky strangers hiding behind a cloak of anonymity on social media. It’s even harder when your mother is Christie Brinkley, one of the most iconic faces of the twentieth century, whose loveliness as a model and as a humanitarian was often overshadowed by the tabloids’ fixation on her four marriages and the drama surrounding their implosion.

So if Sailor Brinkley Cook, whose father is Hamptons architect Peter Cook, had chosen to act out, as so many children of fame have done before, it would be understandable. Instead, for someone turning 20 in July, she’s grounded. Shaped by her small-town upbringing on the East End. Focused on a future she fully aims to succeed at on her own terms. And painfully, poignantly honest about the body-image issues that nearly ruined her health and her spirit.

“I think it’s because I grew up in Sag Harbor,” she explains. “I loved how quiet and small it was, once the summer people left. You’d think that I’d have wanted to move to the big city—my mom kept wanting to move to New York—but I was the one who wanted to stay.”

Now a West Village resident, she’s developed “some of the city mindset of needing things to do and meet people,” she says. “When I go home to Sag Harbor, it’s harder to sleep in the quiet. But after two days, I find myself a lot more centered, and I can fill my days not with business but with enjoying peace.”

Her childhood was spent outdoors, enjoying hikes in Montauk and hours at the beach. “It was bliss,” she says. “The people in the community felt like family. My friends and I would go to grab food at the local café and know everyone serving us.” She attended the Ross School in East Hampton, where she was encouraged to pursue her interest in photography. “They taught me how to think outside the box,” she says. “They had a spiral curriculum, and it was centered on doing my portfolio for college. They created classes for me in analog and digital photography, postproduction videography, and independent studies with my photography teacher.”

Her work paid off. Sailor has spent the last two years at the Parsons School of Design, one of the premier art schools in the country, studying not just photography but integrated design, which focuses on fashion, sustainability and entrepreneurship. These are subjects dear to her heart, as she’s demonstrated with her volunteer work for Smile Train, which provides pro bono surgery to children with cleft palates, and UNICEF. “I started doing lemonade stands in Sag Harbor when I was five,” she says with a laugh. “I’d make about fifty bucks a day and I’d send it off to UNICEF. It was really sweet. And I’d love to get more involved with Planned Parenthood and the ACLU.”

She’s also made a tough decision to take the next year off from Parsons, working full-time instead as a model repped by IMG. “I’m taking my gap year now instead of before starting college,” she says. “I’ve talked to a lot of people about it, and for me, right now, the most beneficial lessons I think I can learn are outside of school. Although my generation has been bred to multitask, I find as I get older that I have more respect for doing one thing at a time, even though I haven’t found that one thing at college yet. Which is why I want to be able to explore and go places to figure it out. It’s very liberating to have these opportunities now, and take them when I can and see where they lead me before I go back to my studies.”

Being a model was not the career Sailor envisioned for herself as a child, however, despite her mother’s success. “I had a lot of issues with my body, and I am very open about it, although I only just got that way recently,” she says. “With whatever voice I have, I want young girls not to have to go through what I did with myself, because I was this pudgy little kid, and as I grew older I became more and more aware that how I looked was ‘wrong.’ I was eating well but I have never been stick-thin or bony; I always had muscular legs and hips. My mom was that way, too—models of her generation were a size six or eight and now they’re subzero.

“When I was only 12 I was getting bullied—not by my friends or at school, but by the media and people I didn’t know who told me I was the chubby Christie Brinkley,” she continues. “And I realized that boys didn’t like me. I’d look at magazines and these girls had flat stomachs and tiny arms. I didn’t want to model at the time but I was so insecure that I thought the only way I could ever be secure was to emulate them. Because they seemed so powerful and beautiful and proud of themselves and I wanted to feel like that, not look like that. It was all about getting the attention and all the externals I thought I needed for myself.”

She went on an extreme diet and developed an eating disorder, eating a scant 800 calories a day, never eating after 5 p.m., working out three hours a day, and obsessing about her weight so badly that her hair turned brown and she lost her joie de vivre. “I went down this really dark hole just trying to control everything because I had no control over myself. I got away with it because I still had muscles and didn’t look anorexic, and even my mother didn’t realize I needed help because I was very clever about eating ‘healthy.’ Everyone thought I was normal. Thankfully, I met a really great group of friends who were living normal teenage lives, going to parties and having pizza at 8 p.m. and hanging out, and I wanted to be a part of that so much that it saved me. Instead of freaking out that I was too tired to go for a run, I’d hang out with my friends at the beach instead.

“We internalize so many of these messages and issues with ourselves—even now in today’s climate, which is so much more inclusive and diverse than it was when my mother started modeling—that there’s still this feeling of I’m not good enough,” she adds. “I see a change in myself, and I feel a lot more accepted for who and what I am. Now I can be beautiful and healthy just in myself.”

Which is, after all, what Christie Brinkley was always known for as the epitome of the sun-kissed California girl, glowing with vitality. “She came across like that because she was having fun,” Sailor says, running her fingers through her wavy blond hair and looking, at that moment, exactly like her mom. As she did, exuding that same sense of fun and ease in her own skin, when she posed with Christie and big sister Alexa Ray Joel in the 2017 Sports Illustrated Swimsuit Issue. She stays in shape by running and working out and boxing at Work Train Fight, not far from her apartment in the West Village.

“My mom was enjoying herself, and that’s what I really want to embody for myself—when you do things that make you happy, and when you’re enjoying your surroundings, it shows. It’s so important for young girls to see that, because there’s so much pressure, from body image to jobs to education, on my generation. There’s too much information, especially due to social media, so it’s even more crucial to be spreading messages of inclusivity and to love yourself and appreciate who you are. When I was growing up, I had my friends and my own little world in the Hamptons. Now, there are 700 worlds—on Twitter, on Instagram, on Snapchat. What’s so crazy is that these young people look at these lives and how a happy person looks and wonder why their lives aren’t like that. But’s it’s just a highlight reel. My own Instagram is a highlight reel. I’m not posting when I’m crying!

“I’ve always had a hard time with balance,” she adds, “because I want a lot of something or nothing, but now I’m going to try and balance both. I want young girls to look at me in magazines and think that they can be my friend or wear what I’m wearing or live the life I’m living. I see myself as a normal person and I surround myself with normal people. If I turn into a bitch, just slap me!”

No chance of that happening. For now, as she’s about to embark full-time on a career that started with a spread in Teen Vogue when she was 15, Sailor has her feet firmly planted on terra firma. “I can’t believe people actually recognize me and want to take a picture,” she says with a laugh. “Because there are some people I don’t want to meet because I love them so much. Like Diane Keaton. I love her so hard that it’s easier for me to stay away from somebody—it’s too hard to be around people whom I adore. I just can’t! The same thing happened with Gloria Steinem when I was right next to her at an event and I couldn’t say anything to her because I was so intimidated. And then I went to Art + Commerce, and I met photographer Cass Bird there, and I’m such a huge fan. All I could do was mumble how great it was to meet her and then hurry away!”

She doesn’t need to worry about getting recognized at her favorite secret hideaway in the Hamptons dunes—if you can find it (and she’s not telling!). “All I’ll say is it’s on the left side of the Montauk Highway,” she says with a coy smile. “No one is ever there, and it’s almost scary because you’re just alone with nature and deer and rabbits, and it’s like being in the Sahara Desert. I feel much more accomplished if I spend a day in nature than in actual work.”


Photographed by Ben Fink ShapiroStyled by Erin Walsh


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