How I Shop: Caroline Vreeland

The musician talks about the legacy of the Vreeland name, her new album "Notes On Sex And Wine" and why what you wear under your clothes is the sexiest of all.

We all buy clothes, but no two people shop the same. It can be a social experience, and a deeply personal one; at times, it can be impulsive and entertaining, at others, purpose-driven, a chore. Where do you shop? When do you shop? How do you decide what you need, how much to spend and what's "you"? These are some of the questions we're putting to prominent figures in our column "How I Shop."

A lot can change in six months, and no one knows that better than Caroline Vreeland. In the half a year since we've initially spoken, she's broken up with a boyfriend, moved from Miami to L.A. — though she's also contemplating a jaunt in New York City — worked on a A.S.M.R. story with the Moxy Chelsea hotel, released the first music video and single from her forthcoming album and collaborated on a capsule collection with Kiki de Montparnasse, exclusively carried through Farfetch.

But what hasn't changed is Vreeland's commitment to music. Farfetch celebrated her collaboration with Kiki de Montparnasse at The Box in New York City, accompanied by a performance of some of her new material, including a rendition of Cher's 1966 hit "Bang Bang (My Baby Shot Me Down)" and the aforementioned new single, "Stay Drunk With Me." Vreeland belted out the sultry (and often wine-inspired) tunes in a silver one-shoulder, dip-dye dress, another-Kiki de Montparnasse creation. She added that she was wearing the microphone thong from her collaboration — because the night was all about what's underneath, after all.

Vreeland has done other partnerships, but hasn't delved deep into doing any designing in the fashion arena, so this is very much a first. "I didn't think lingerie would be the first thing, but now that I'm looking at it in hindsight, it's the perfect fit," she tells Fashionista at The Box, draped in a very luxurious satin robe. The collaboration with Kiki de Montparnasse started when Vreeland wanted to borrow a dress from the brand. "I really think the way they elevate sex to be chic and elegant as opposed to a taboo topic that's hush-hush always turned me on about the brand," she says.

She met its VP of Design and Production, Jose Velasco, and a budding friendship soon turned into conversations about ways to work together. "The first thing we talked about doing was a bra, because it's not really the place for my big breasts," she says. "Even though their pieces are really beautiful and elevated, they don't have bigger cup sizes — not many brands do. He told me he wanted to expand and felt I was the right person to do it. I was over the moon because that's my wheelhouse; for better or worse, I've got these big boobs."

But bras take a lot longer in the production realm and it would've required Kiki to create a different shape than they've ever done before. So instead, the discussion moved to panty styles. They settled on five "Caroline-isms" for the embroidered thong and bloomer styles. "We did pasta, obviously, because that's the root of life, the wine because I'm lit AF and my single is called 'Stay Drunk With Me' and I'm obviously a wino, and cleavage too big for a bra," Vreeland explains. "Then we did the lipstick and of course, the gloved hand holding the microphone, which has an edge because the glove is latex."

That wasn't all Vreeland shared; she also imparted her wisdom on all things shopping, going for that big ridiculous splurge while traveling, how she's working with her stylist to elevate her aesthetic and so much more. Read on for how she shops:

"I definitely feel like I take on characters, but they all come from the core of who I am. So when it comes to shopping, I don't necessarily want to change who I am. Fashion allows me to explore different sides.

Music has always been the number one thing I've done: I've been singing since I was eight years old. I did a music video for my song that I released last year, 'Unbreakable Love' and the stylist on set, Henry de Castillon, took two red leather gloves and taped them around my neck like a necklace. The way he approached it…he was mixing vintage with Missoni and Off-White. Sometimes we have to shoot an image that's a full look and I understand that, but he didn't see it that way. He looked at my body and my personality. After the shoot, I asked him if he'd be my personal stylist. After I hounded him and he gave me, 'Oh, I am not sure if I can do this,' ultimately he said yes.

Even though I have the Vreeland name and I'm very thankful to have it, I come from humble beginnings. I moved away from home at 18 and I was working at nightclubs, restaurants and bars — everything to make ends meet. I've never been in a position where I could pay a stylist. But now that I have so many events and different projects, it's been so helpful to have someone who handles it for me and who knows my body, my measurements and is innately chic.

We don't base our decisions on whether it's couture or not, or Fendi or not. That's not interesting to me. What is interesting to me is that first, a designer wants to work with me. I've been lucky to be invited to some really big fashion shows and work with some really big brands, but it's not a given that they'll always dress me. I'm still working my way up. So if someone wants to offer something to me and they're not a huge name, I think that's awesome and I want to promote young, up-and-coming designers.

And even though I love Miu Miu, Prada, Chloe, Alexandre Vauthier, I can't afford to buy clothes from them. Maybe a one-off moment or an accessory here or there if I'm treating myself. But what I can do, and what Henry is teaching me, is to recreate certain silhouettes. Not to steal it, but to mimic certain shapes because you can do it with a cheaper price point.

I don't go into stores too much, but I do go into What Goes Around Comes Around in New York City the most. They're so attentive there and they really sit with you — I spend hours in there. Of course, if it's vintage, you have to sort through everything. I feel like stuff from the '60s, which was cut so differently, fits my body better. When I want to treat myself, I go there. I'm very impulsive and I'm very crazy with my shopping. I shop from the heart.

I'm that girl that if you're in the Bahamas with me, I'll say, 'There's that Jacquemus hat, I'm going to bring it home.' It literally won't fit through the door of the plane, but I'll ask the airline to find a way. Tie it to the roof, because we're taking it. Or I'll find a shoe with a ton of plumage on it that I'll sit on my lap on the plane home from Europe. If you see something in the world and it's going to remind you, when you bring it into your home, of that time and traveling there, I feel like that's so important to have. It's really not about being reasonable. It's about having beautiful things that you love.

The thing I remember most distinctly when I was growing up was having no fear. A lot of people ask me about my relation to Diana Vreeland and it may sound cliché, but I think even just knowing her as a woman and being related to her, I have this ability to take risks. I remember my mom telling me she wouldn't go to the supermarket with me if I was wearing four-inch heels. But I was never afraid to be taboo, do the most, and be extra.

I was so lucky to be welcomed into this whole world of fashion because of my great-grandmother and I would never bite the hand that feeds me because it's an incredible legacy. I own it and I love it. People cry to me on the street and tell me she changed their lives — that's big. When my name became recognizable, it was only in that vein. And that's my bad too, because I fell into it and went to fashion week. I loved it and the relationships I have with brands and designers are things I wouldn't trade for anything in the world.

I always opt for a Palmer girl-kind of makeup look. I wouldn't say that I'm as adventurous with makeup now as I used to be. Skincare is a little more important to me now than makeup because I am in my 30's. That's what I'm excited about now — prevention most of all. I've started to do the Clear + Brilliant laser, which I try to do as much as possible. Thank God I'm in the position where I can promote and have other people come in exchange to go, because it would be really pricey to do that myself. I'm trying to think about the future of my skin a bit more. But what's been exciting for me is fragrance, because since my sister is doing social media for the Diana Vreeland fragrance, she's been opening my whole world; she's the nose of our family.

Is it boring for me to say a good sex life and a healthy appetite make you look good? I've been really obsessed with Augustinus Bader The Rich Cream. And also the GCDS lip balm. It's dark green, but it has the same result as the Dior balm which you put on and it turns your lips a natural pink color. When I'm just wearing SPF and I want to look pretty during the day without wearing makeup, I'll just wear that, Glossier's Boy Brow, and call it a day.

I just found out that I'm going to open up for my friend's band on their tour, end of February, beginning of March. It's just a few cities on the East Coast, but it's a real thing. I have no idea how we're getting there, but I feel like I'm going to be a real artist. I might have done cool covers and worked with cool photographers, but the fact that I'm going on a little tour on the East Coast, that to me feels like a big accomplishment. I've had to really prove myself. And it's cool to be here because the last time I was at The Box, I was kicked out."

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