How Caroline Vreeland became the gutsiest scion of fashion royalty while honoring her lineage, cherishing her body and bringing an unapologetic sexiness to the 305.
When Caroline Vreeland (nee Zickerick) was 8 years old, she landed the role of a lifetime. Not Snow White or orphan Annie or sleeping Aurora. Those would be too easy, too pedestrian. “I was cast the role of the wind,” the 30-year-old singer, model, actress and all-around Instagram juggernaut tells me on a bluebird August morning, the kind Miami is famous for.
True, there were a few minor complications with being cast as the wind. For starters, the wind didn’t appear onstage. “I was backstage holding a mic, blowing into it,” she says. For some kids, being cast as the wind, stage left, would serve as a humbling experience, or a moment when other pursuits suddenly became more attractive. But not for this kid. Not Caroline. “There I was blowing into this mic, and I suddenly realized, "I'm killing this. I sound great."
Sequin dress, $3,330, by Balmain at Saks Fifth Avenue, Brickell City Centre; hoop earrings, price upon request, at Pinkgun Gallery.
And she wasn't wrong: a few weeks later, she scored a coveted spot with Raz Kennedy, the premier vocal coach in San Francisco who has worked with singers from Counting Crows, Third Eye Blind and Talking Heads, among others. She studied with him for a decade and in August this year launched her first widely released album, Like a Woman, Like a Drunkard, Like an Animal, a six-song triumph of bluesy, soulful croons. “Music has always been my driving force,” she says. But let’s go back a second. We'll get to all this later.
Vreeland was born and raised Caroline Zickerick, the daughter of iconic Vogue editor Diana Vreeland’s granddaughter and a German diplomat. (That makes her DV’s great-granddaughter, just to be clear.) When her parents divorced early in her life, her mother moved her and her younger sister into an affl uent Bay Area neighborhood. “My grandparents lived there, and we didn’t know where else to go,” she recalls. It was a humble beginning of sorts. “All our friends had BMWs and Hummers, and we all slept in the same room. I didn’t want for anything, don’t get me wrong—we had a really nice little family unit, us against the world—but we weren’t rolling in dough.”
From the start, while she didn’t share her famous great-grandmother’s name, she shared her inimitable independent streak. When her sister sneaked out of a friend’s house to go to a party, she was “sneaking in to eat the fried chicken her dad made,” she says. “I was the weird one.” But she was also the equitable one, the just one, the head of her high school’s gay-straight alliance long before that was a trendy thing to do. “It felt really important early on to be an ally to the gay world. I found myself as the one standing up on the bus telling people in the back not to use the F-word. For some reason, it became a part of what I wanted to champion. I always felt safer and more understood, appreciated and welcomed by the gay community,” she says. (As an adult, Vreeland has dated both women and men.)
After high school, though, Vreeland wanted out. “I didn’t take the SAT; I didn’t go to college. I was like, ‘I need to do music, music, music. I’m gonna get out of this town as quickly as I can, get to L.A. and start my life,’” she says. And that’s exactly what she did the second she turned 18, working retail and in nightclubs and bars to pay her rent and finance her art. And because she’d never felt particularly close to or supported by her father, she also took her mother’s last name, at first somewhat reluctantly. “I was working on different musical projects, being signed to labels, being dropped, being signed, the same story a lot of musicians go through,” she says. “I was so adamant and stubborn about paving my own way, making music the reason people cared about me and not using the Vreeland name to get my foot in the door. But then I realized this name has so much power, and I’ve started to honor it.”
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Honoring that name meant inhabiting the world of fashion, the very world her great-grandmother helped build. In her late 20s, Vreeland signed with a modeling agency and did the damn thing—her way. “I wasn’t readily welcomed into the fashion world physically. I was because of my name, but my body…” Her bust falls decadently and deliciously outside of sample size—she’s a natural 32F, if you must know. She describes a swimwear shoot early in her career: “All of a sudden we’re shooting, and this photographer is like, ‘Honey, I can’t shoot you; I can’t work with this body. I can’t work with these boobs.’ So I literally had to shuffle down the driveway and leave the shoot.” At the time, the feeling of being body shamed was shocking; after growing up “flat,” Vreeland developed at 18. And she was proud. “I felt this power within me. I cherished it; I worshipped it. I didn’t find it to be shameful.”
She’s since carefully chosen to work with brands that support inclusivity. Carine Roitfeld of CR Fashion Book made her a coveted CR girl, photographed her in a custom Alexandre Vauthier bra, and then signed her up as a sex columnist to cover topics like threesomes and cunnilingus. “It’s been very uncharted territory,” says Vreeland. (Kind of. Diana was a columnist too.) “I’ve always loved writing and reading, but I haven’t shown that side of me. People see me as a fashion girl. They see me sitting at fashion shows and working with brands. People don’t want you to be many different things.” The thing is, as she’s come to find out, that’s exactly who she is—undefinable, unpindownable, versatile and expansive—in every strand of her DNA. But make no mistake: Music is and has always been her lifeblood. Which brings us back to her album, which she wrote single-handedly and from the heart. (The title is a line from The Fountainhead, which she read this summer; a tearful Instagram video to her 320K followers shared how moved she was by the text.) As for her aspirations with the album? “Yes, I want to be the biggest star in the world,” she says with a laugh. “But the drive for music is because I have no other outlet, no other way to channel my pain or the different things I’ve gone through. And I’m just grateful that I have a creative way to do that.”
Black pleated leather dress, $4,875, waist belt with gold buckle, $1,275, Medusa Tribute leather choker, $3,195, Medusa Tribute leather bracelets, $2,550 each, pearl Medusa ring, $295, Tribute Donatella coin ring, $260, and crystal fringe boots, price upon request, all at Versace, Bal Harbour Shops.
But the music isn’t all angst. There are love songs too because, yes, Vreeland is very much in love. That’s how she found herself in Miami and on the cover of this magazine. For the last few years, Vreeland’s been dating Jason Odio, the restaurateur behind Sidebar, Ariete and Baby Jane. The two met years ago when she spent six months making music here. They reconnected and did the bicoastal thing, which was great—right up until it wasn’t. “When I started thinking about moving to Miami for a man, for love, it felt scary,” she says. “But then I realized it shouldn’t be. If I want to come here to be with him, it’s my choice. I go where I should go, and this is where I am now.”
And perhaps unsurprisingly, it’s here in Miami, a city of effervescent nightlife, unparalleled beauty and rich community, that she’s found herself feeling more at home—and more herself—than ever. “I’ve been so transient. I’m so grateful for that, trust me; I love it. But I’m starting to feel the itch. I want to put down roots. I want to get a house. I want to hang art. I want to have a plant that doesn’t die. I have that yearning in me. Miami… it’s perfect for that new chapter, that new place, to start that kind of life.”
Photography by: Photography by Camila Rios; Style by Danny Santiago; PRODUCTION by EDDIE FRANCO AT E11EVEN; video by DAVID SIQUEIROS; Hair by Danny Jelaca at Creative Management @ MC2 using Balmain Hair Couture; Makeup by Mariana Hernandez