The Transformation Of Cindy Crawford: From Supermodel To Entrepreneur To Queen Of The Playa

Photo Credit: Brian Bowen Smith

 BY LAURA SCHREFFLER

PHOTOGRAPHY BRIAN BOWEN SMITH

STYLING BRAD GORESKI

HAIR DIMITRIS GIANNETOS

MAKEUP LISA STOREY

NAILS YOKO SAKAKURA

SHOT ON LOCATION AT THE SANTA MONICA PROPER HOTEL, SANTA MONICA, CALIF.

Photo Credit: Brian Bowen Smith

LET’S PUT IT THIS WAY: there are very few things Cindy Crawford hasn’t done. As a 30-plus-year modeling vet, one of the OG supermodels, a trailblazer who defined a pivotal moment in time when fashion models became stars in their own right, she’s basically seen it all, done it all, and done it all again. But, up until early September, there was one thing she hadn’t really tried: living in the moment, free in her own skin, forgetting time, place, and beauty routine. Which is how, at age 56, she found herself on a bicycle at Burning Man, cycling through a sandstorm and covered in white dust, shining like a beautiful beacon in a shimmering gold jumpsuit, living her best life.

That said, a surreal desert counterculture party in Nevada’s Black Rock Desert is not the place one might expect to see the impeccable Ms. C, but in her opinion (though said rather more succinctly), to hell with what everyone else might think — she wanted to go. “[My daughter] and I got invited by a friend of ours, kind of at the last minute, and we were like, ‘Why not?’ It just seemed like the perfect thing, because we were tagging along with people who had been there before, so we didn’t have to figure anything out except what to pack, which — by the way — was already intimidating enough. [FYI, she nailed her trade, likely outclassing those who gave drugs or daisy chains by swapping for mini bottles of Casamigos, finger lights, and Polaroid cameras.] It was only two days and two nights, so I was like, I can do anything for 48 hours. And it ended up being a really incredible experience,” she admits.

I urge her to explain the experience. Personally, I still don’t quite get what actually happens at Burning Man; its purpose seems vaguely ambiguous, while the concept behind a Playa name makes me think of the drunken alter egos sorority girls gave themselves in college, yet apparently it’s synonymous with a secret self, both gifted at and only used whilst at the festival. (Crawford didn’t stay long enough to get one, but there’s always next year, since she’s already talking about going back). 

“I mean, listen, it’s raw. You’re uncomfortable because it’s dusty and dirty, but it’s very creative, Mad Max meets Alice in Wonderland meets virtual reality. It’s just wild, and very liberating because you’re outside of yourself, in a way. It’s not like, ‘Oh, my outfit looks good, therefore I feel good.’ I’ve only had an experience like this once before, when I stayed at an African game park for a month; I literally only had a tiny hand mirror that I could use to brush my teeth. Like then, the way you looked here did not determine how you were feeling that day. It was incredibly freeing.”

In being uncomfortable, in not being able to be the Cindy Crawford, she found a poignant sense of release, and, simultaneously, relief that she didn’t have to be everything to everyone; that, for a brief moment in time, she could just be.

“I didn’t get it before, but now I feel like I do. For me, it was like, you’re so out of your comfort zone in every way, that you have no other choice but to find yourself. We all walk around in reality having stepped into these roles — mother, wife, whatever — which are all roles I signed up for, but there is stuff that comes with those roles, like responsibility. In my family, for instance, I’m the organizer, I’m the on-time one, I’m the more serious one. And I think it’s easy to get caught up in these roles, and to feel introspective as a result. Like, who am I? I don’t know. Maybe I’m just going through a midlife crisis,” she laughs ruefully. (Here I must disagree: if she was really going through a midlife crisis, she would have definitely worn a hot pink unicorn bikini to the Burn; instead, it was the aforementioned gold-flecked jumpsuit, a modest black bikini top, and ski goggles.)

But, for a brief time, at least, she was able to discard any uncertainty, doubt, or agenda, like a snake does its skin, releasing and unleashing in the dusty desert air. “I think when you’re at Burning Man, you shed those skins, and you’re just you. You’re your own essential being. I feel like it’s a great place to just reconnect with your true self,” she maintains.

Photo Credit: Brian Bowen Smith

As it happens, it was also a great place to connect with her daughter. It’s unbelievable, yet also a spectacular testament to Crawford’s character that, when her mini-me turned 21 and wanted to embark on an epic, uncharted adventure to celebrate the occasion, she chose her mom as her ride-or-die. But I guess when your mom is Cindy Crawford, it makes sense; this is a woman who will be forever cool. What she says next simply furthers my point.

“I’ve been very fortunate, because I’ve got to do some fun things with my daughter. We did the Off-White fashion show together in Paris, and it wasn’t as if I was there as her mom or she was there as my daughter — we were both invited to be a part of the show. And then there’s something like Burning Man. I mean, I’m sure she would’ve loved to have her boyfriend there, and I would love to go with my husband sometime, but it worked out that we went together and we had a great time. I love doing anything with her, but you also want to be cautious of letting her have her experiences without mommy looking over her shoulder. For example, she turned 21 [at the festival]. The next night she had a small dinner, which I went to, and then a party at a club, which I didn’t.”

A love of freedom must run in the family: as Cindy herself discovered, it’s essential for her own personal happiness, too.

As George Michael’s “Freedom 90” starts to play in my head (the music video that made Crawford a star and household name), she says it was only when she returned to her everyday life in Malibu that she realized what gift the festival had truly bestowed upon her.

“When I came back, I went God, I feel so carefree and fun, on the Playa, riding bikes, with no schedule. It’s like, ‘Oh, let’s go look at that piece of art,’ and then you’d ride over there, and either stay for five minutes or you stay for an hour. But then, you return to reality, to your life, and I personally felt like now I’m the responsible mother again. I’m this, I’m that. And now, it’s me questioning, at this point in my life, do I still want to be all of those things that I unconsciously signed up for?”

Heavy. I always expected true “Burners” (which is how Burning Man enthusiasts refer to themselves — not to be confused with “burnouts,” but… kind of?) to live in states of heightened reality and to use their time away from reality, from cell phones, from normality, as an escape. But Crawford, one of the most iconic models in history with the longevity to back it up, doesn’t fit the mold of who I expected to attend, or one who would get so much out of the experience, for that matter.

And while it made her question her everyday reality, Crawford is hardly a fool. Actually, one might say she’s the complete opposite, having been valedictorian of her hometown high school in DeKalb, Illinois, earning an academic scholarship to study chemical engineering at Northwestern (which she attended for only one semester before dropping out to pursue a full-time modeling career). As such, she strategically decided to figure out how to implement her epiphany of self-discovery into her daily life at home.

“I started reevaluating. I was like, wait, I had so much fun. I felt carefree there. How can I bring that back to real life?”

For most of her life, Crawford has been the consummate scheduler, the ultimate planner. She’s needed to be to get to where she is today, to have the kind of career longevity that’s eluded so many. And she loves her life, she does. She’s content, the kind of woman that has it all. But spontaneity has never seemed like a luxury she could afford. Time (a familiar topic, given that she’s timepiece brand Omega’s longest-standing ambassador) always seemed too fleeting. Until now, that is.

“It’s something I’ve been working on,” she says. “I started working with a coach this year, and one of the things that she speaks to me about is time. Specifically, where do I feel constricted, and where is it stressing me out? I’m a planner, and very, very organized; I’m the type that gives myself exactly the amount of time I need for any specific activity. Let’s say I finish my workout at 9:30, and have my first call of the day at 10, so I have a half-hour to shower and get myself together. But, say, my husband wants to have a conversation with me. I found that I’d be looking at my watch, like, I have three minutes, and then he would get irritated, or I would feel the stress of knowing that now I wasn’t going to have time to put makeup on. It never occurred to me to maybe push my first meeting back a little, because I was just so focused on being efficient.”

She continues, “For so long, the only way for me to do everything that I wanted to do was to pencil it in. For instance, I always enjoyed being the first one up in the house, even when my kids were little, because I needed that 20 minutes where no one needed anything from me. So I would get up early and have an outdoor Jacuzzi, put on gym clothes, and get on my email. Taking that Jacuzzi meant that I had taken the time to connect with myself. I never really scheduled in unscheduled time, and I think I’m doing more of that. Now, I’m finding ways to give myself more breathing room. And that’s where I’m at in my life, leaving a little bit more cushion for the unexpected.”

And more time to explore the freedom that comes with it.

Photo Credit: Brian Bowen Smith

WHEN I NEXT TO SPEAK TO CRAWFORD, it’s the day after our photo shoot at the Santa Monica Proper Hotel, and she’s low-key and beachy at home in Malibu, relaxed and make-up free — a chameleon-like departure from the glamazon of yesterday in all of her high-heeled, sultry glory. But personally, this Cindy is the one I prefer. Right now, she’s both down-to-earth and self-deprecating, someone you could hang out and have a few margaritas with. Professional, shoot-mode Cindy Crawford, dressed to kill in Dior and Chanel, with fierce makeup and five-inch heels (bringing her height from 5’9” to 6’2”), is intimidating as hell.

Which brings us to the topic du jour: confidence. Looking as she does, it’s only natural to assume she’s always had it. And she has, but that doesn’t mean she’s always been secure, nor would it be fair to assume she doesn’t have the same self-criticisms, even though she’s outrageously beautiful. As someone who has literally come into her own in front of a camera, the hyper-judgement of others, of strangers, is very, very real.

“I was never full of self-loathing or anything like that. I was probably a typical kid,” she says now of her youth in Illinois and just after, in 1986, when she moved to New York to model professionally. “But,” she notes, “modeling is interesting, because all of a sudden you have a seal of approval that other people think you’re attractive, though you know the reality of the smoke and mirrors that go into making pictures. So sometimes, I felt that if people saw me in real life, they’d be surprised. And even for myself, I’d wonder: do I need to be Cindy Crawford tonight, or can I just be Cindy? Because I need two hours of hair and makeup to just be Cindy Crawford, or at least be presentable.”

Luckily, the opposite is true in her private life. After a day of full glam, she’ll head home to husband Rande Gerber, he of Casamigos fame, who likes her just as she is — a bare-faced beauty with nothing to hide. “He’ll say, ‘Wash your face; I like the way you look without makeup.’ Which is nice,” she admits, though says that personally, she feels much muchier with a wee bit of war paint than without. But overall, she faces industry pressure daily, especially when someone describes her as “ageless.” While most would love such a description, for Crawford, it’s an ongoing reminder that she is not. (Though here I must disagree too, but I won’t use the “a” word given that she doesn’t like it.)

Photo Credit: Brian Bowen Smith

The euphemism behind aging gracefully was, in fact, the impetus for creating Meaningful Beauty, the skincare line she co-created with Parisian cosmetic surgeon Jean-Louis Sebagh in 2001 (which is re-launching a line of haircare products next year, inclusive of existing items like a shampoo, conditioner, detangler, and scalp spray, as well as a new serum). “It’s funny,” she muses. “Even in my Meaningful Beauty infomercial, they used to say, ‘She hasn’t aged’ and they would show side-by-sides. And I’d tell them to stop, because it puts too much pressure on me. I know all the ways that I’ve aged. My face has gotten much thinner; my mouth isn’t as full. Being told I’m ageless isn’t right, especially because getting older is hard enough, never mind that we live in a youth-obsessed culture. So in that sense, the things I’m trying to make Meaningful Beauty about for other women are the things that I have to remind myself about, too. I’m not 25, so why should I be trying to look 25? Why do I want someone to mistake me for a 25-year-old? I’ve had children. I have all this life experience.”

What’s more, she’s proud of herself for letting that life experience play out behind the camera, even if she doesn’t always like what she sees. “When I started modeling, I said, What am I going to do after I turn 25? There wasn’t someone who had a career like me before that I could follow or look up to,” she recalls. “And then, all of a sudden, I was still modeling at 26, 27, 30, 35, 40, and now, 56. There was no way I thought I would still be quote unquote ‘modeling’ to this day. And even though I’m not in front of the camera nearly as much as I used to be — nor do I want to be — any time I get my picture taken, even if it’s just on an iPhone, I’m striking a pose. You can’t unlearn that. So I’ve learned to embrace the different stages. I’m not 56 trying to do the same jobs that I did when I was 25 and 30. I’ve evolved, and the businesses that I have have evolved, too.  [These include her hugely successful Cindy Crawford Home collection, which grosses over $350 million annually in retail sales; successful book releases such as Cindy Crawford’s Basic Face and the 2015 The New York Times bestseller, Becoming; global, long-term contracts with brands such as Omega, Revlon, and Pepsi; and the upcoming AppleTV+ docuseries The Supermodels, alongside her fellow icons Naomi Campbell, Linda Evangelista, and Christy Turlington]. I think that’s why I’ve had such career longevity, and why my audience will follow me — because it feels authentic and it is authentic.”

This bid for authenticity is a big part of the reason why she continues to model today. “There’s one comparison I use a lot, and it’s this: I’m like an aging athlete. I know the game so much better, but I don’t have a 20-year-old neck or whatever. Sometimes I think, screw it. Maybe I don’t want to model anymore. But then I think, gosh, then I’m just further telling women that at a certain age, we’re just expired, and we should go on the shelf. Do I want to play into that for women? And so I don’t. Even though sometimes I don’t necessarily feel as confident, or if I see a pictures of me and there are things I don’t like, I still think yeah, but that’s real. Aging is what happens if we’re lucky; it means that I’m alive.”

And really, isn’t that more, well, meaningful than anything else? To be living, yes, but, in a more philosophical way, actually enjoying being alive, living in the moment? Crawford thinks so, and clearly, she’s doing her best to embrace that ethos right now. And so she reminds herself, while sharing with me, what the phrase ‘meaningful beauty’ really means to her. “The name, and the intention behind the name resonates even more now than it did then. Because, really, what is meaningful about beauty? Why does it even matter? [The answer is] because it gives us confidence. It’s not about beauty, per se, but how you feel. Maybe it gives you a little more energy, makes you a little more outgoing, maybe it makes you more willing to ask a question or take a chance.”

Photo Credit: Brian Bowen Smith

On that note, it feels like the appropriate time to remind Crawford that she nearly broke the internet earlier this summer when she posted an Instagram photo of herself in a Melissa Odabash bikini, a thank you to her designer friend for the suit. “The beauty of having your own social media is that you get to curate. Like, I look pretty good in this picture; I’m going to post it.” She pauses, and says, “I’m probably at an age where I should be wearing one-pieces, but I’ve never worn one-pieces, and it’s [the same kind of dilemma I have with my hair]. I’ve always had long hair; I wouldn’t feel like me with short hair. And I’m kind of worried, like, oh, God. Am I going to have to cut it when I get a little older? Am I too old to have hair this long? [Similarly], whenever I put a one-piece on, I don’t feel like me. And there might come a point where I do have to wear one; I do have a few in my swimsuit drawer just in case it comes upon me one day.”

There’s no should when it comes to fashion, and Crawford knows that far better than I could. Nor are there any rules as to what one should and shouldn’t do dependent upon their age. I find there’s something liberating about her refusal to cede her love of bikinis or her famously long locks in favor of something more traditionally “age-appropriate” (because what does that phrase even mean these days?); in owning that sometimes, in order to feel good about yourself, a little app-induced retouching is necessary. (“You do a little FaceTune once, and then you think, how did I ever live without it?”); and that it’s okay to be all IDGAF, like she was at Burning Man. “There’s certainly no retouching there,” she says dryly.

“There was a dust storm, and by the end of it, I had white eyebrows, white hair, and white dust had stuck to my upper lip. It’s kind of impossible to take yourself too seriously when you’re covered in dust.”

As we prepare to part ways, I tell her that her life sounds pretty beautiful, dust-storm induced graying aside. Her response is one of the truest things I’ve heard to date. “Life is life,” she says simply. “And that’s something else I’m working on: not characterizing things as good or bad. It’s just life, right? We tend to be like, ‘life’s so hard’ or, ‘life’s so great’ — but it’s just life, all of it.”

“The good, the bad, the ugly, and the beautiful,” I say.

“Yes,” she agrees, “but I appreciate the raw and the ugly, too, because it’s real.”

She smiles. Scheduled though it might have been, it’s still her time, and she knows exactly how she’s going to use it. “Now, I’m going to get into my Jacuzzi.”

I think Cindy Crawford may have just found her Playa name. 

Photo Credit: Brian Bowen Smith