With a new documentary series announced alongside her fellow supers, Cindy Crawford reflects on why she’s still in the game, 40 years into her exceptional career.
When Cindy Crawford’s Zoom shot pops up on my screen, she is wearing a pretty, powder blue sweater and no discernible makeup. It’s 11am in Malibu, where she lives, and she is right on time. “The only advice I gave my kids when they started modeling was be on time, stay off your phone, and be prepared,” she tells me. Crawford’s face, especially for people of a certain generation, has been an integral part of the cultural landscape for almost four decades. The famous beauty mark, the Pepsi commercial, the George Michael Freedom! ‘90 video, the hundreds of magazine covers: Cindy Crawford is more than a model – she’s earned a spot in the pantheon of instantly recognizable icons; what a marketing executive might call a “powerhouse brand.”
Dress, hat, Schiaparelli; earrings, Oscar de la Renta. Photo: Thomas Whiteside
Achieving supermodel status along with the likes of Christy Turlington, Naomi Campbell, Linda Evangelista, Claudia Schiffer, and only a handful of others is one thing, but maintaining the same level of fame 40 years into the business is another. “Everything came together in a way that was bigger than anyone individually. It was a time when one plus one plus one equals 1 000,” she says about why being a fashion model, once a quieter and more fleeting job, gave that particular group of women their lasting superstar status. Later in her career, Crawford made a deliberate choice to build her brand by taking daring professional risks, especially for her time. Her flair for business and an understanding of how to appeal to a wider fanbase transcended the world of modeling. Suddenly, star models like her were using their voices, quite literally. She made an exercise video, hosted the MTV show House of Style, and wrote a make-up book. “Then I started a skincare line with Dr Sebagh and slowly took more ownership of my career, and I had more of a say in how I was being portrayed.”
In the iconic Pepsi commercial in 1992.
Crawford’s desire to be in control of her professional destiny comes up often during our conversation. In an industry where women are objectified, and there is concern over how some younger girls can be exploited, Crawford says she took the reins very early in her career. “I was doing Vogue and Revlon and then I did Playboy, and people couldn’t understand why I would risk that. It wasn’t about the money because I barely got paid for the first time,” she tells me, running her hand through her famously thick mane of hair. “I gave up getting paid in order to have control, so that I have approval of every image.”
For the cover of the January 1990 issue of British Vogue, Peter Lindbergh photographed Cindy Crawford with fellow supers Naomi Campbell, Tatjana Patitz, Christy Turlington, and Linda Evangelista.
The result was an atmospheric, multi-page, black-and-white spread shot by famed photographer Herb Ritts. “Because I took a chance there, it opened me up to a much broader audience, male and female, which Vogue didn’t have. And that’s why I got MTV and that’s why I got Pepsi.” Those projects earned Crawford a place in the collective consciousness that endures to this day.
Crawford was a supermodel before the age of social media, but it’s social media that may have played a role in bringing back the glam of the Cindy-Naomi-Linda-Christy era, introducing it to a younger generation. There is a nostalgia about that time, as well, right before the internet and smartphones took over our lives, when everything seemed simpler and the pressures of maintaining a public image were less acute.
The four women are working on a documentary series for Apple TV + on the supermodel era due out later this year, Crawford tells me, reuniting for the first time in person in many years. “Two weeks ago, we were all on set, shooting together. It’s been a long time since the four of us were together in front of the camera and it was amazing. In a weird way, it was like no time had passed and, in another way, we also were fully our adult selves.”
Dress, Oscar de la Renta; earrings, Van Cleef & Arpels
When Crawford and I connect, it is the day after her birthday. “My first day of being officially 57,” she tells me as we discuss aging and the inevitability of our faces and bodies changing with time. Does she feel as much pressure as the rest of us to continue to look youthful? “The only way I think about that is, look, I don’t look the same way that I did when I was 25. I’m very aware of that. And thank you to all the trolls on Instagram who love to point that out,” she says laughing. “What I don’t want to do is be part of that message that’s telling women of a certain age, ‘You got to hang it up now.’ Like, why? Again, I’m not trying to be on the cover of Sports Illustrated. I do understand that there’s a season for everything, but I don’t believe in a season of invisibility. So, that’s maybe where I feel a little bit of responsibility to, like, just show up.”
Crawford married businessman and former model Rande Gerber in 1998.
Born Cynthia Ann Crawford in DeKalb, Illinois, in 1966, Cindy Crawford started her modeling career while she was still in high school. She was a gifted student, earning a scholarship to study engineering at Northwestern University, but dropped out after one semester to pursue modeling. She quickly went from working with photographers in her native Illinois to New York, to the international runways and covers that made her a household name all over the world. Along the way, after a high-profile marriage to actor Richard Gere, Crawford married businessman and former model Rande Gerber in 1998. They share two children, Presley and Kaia. Both have chosen to pursue modeling careers and 21-year-old Kaia, who’s fast become one of the most in-demand models in the world, is also trying her hand at acting. Does knowing the pressures of the industry change how much she worries about her kids? “Every mother worries about her children’s physical safety, their mental health, their relationships, their self-esteem. I think the one thing that was different for me is I didn’t grow up in a well-known family, and I didn’t have as much public pressure on me.”
The MTV music awards in 1992.
Public pressure for the kids of established celebrities comes in many forms, most recently with the debate over so-called “nepo babies,” the offspring of stars sometimes accused of having unfair advantages in the entertainment industry thanks to the connections of their famous parents. Crawford’s daughter Kaia herself acknowledged in a recent interview that having a supermodel mother certainly did not hurt her career. Crawford tells me she doesn’t disagree with her daughter, but says that even though celebrity children get a head start, they are still expected to perform. “They come out of a gate and everyone’s eyes are on them,” she says. “Maybe they are given the opportunity over someone who doesn’t have the same advantages, but if they don’t have the goods… If she wasn’t selling or wasn’t creating excitement around collaborations or brands – she does that – she wouldn’t still be working.”
Dress, Tom Ford. Photo: Thomas Whiteside
The wonderful thing about the longevity of the 90s supermodels is that women now have a real-life example of middle-aged bombshells who are still paid to be the faces of cosmetics brands and appear on magazine covers. We may not have their bodies or their looks, but hey, we tell ourselves, we can still be considered desirable as we age. I tell Crawford that this type of representation matters and that perhaps she has become an inspiration to a whole new generation of women. “Do you feel like a role model in that way?” I ask her. “I think if I thought about that, it would actually probably limit me because I would put too much pressure on myself,” she says. “I think more about how do I keep growing and learning and evolving for myself?”
Dress, Carolina Herrera; shoes, Jimmy Choo; earrings, Van Cleef & Arpels
It’s something Crawford has thought about more since the Covid lockdowns, that period during which the entire world seemed to be going through an existential recalibration. Perhaps this triggered some sort of desire to take stock for Crawford, who has worked since the age of 17. “I read a book called Bending Reality and I really liked the author, who is a coach,” she tells me. “The work that I’ve done with her is more like, let’s get back to your 16-year-old self. Like what dreams did you have? Because we kind of figure out what we’re good at, but maybe it’s not necessarily what lights me up the most. I still feel good, I still have a lot of energy. I still feel like I have a lot to offer. So, I want to be doing things that really turn me on.” She says the break that the pandemic forced everyone to take made her want to explore parts of the world that are still on her “bucket list,” including some in the Middle East. “The only place I’ve really been is Dubai, and I’ve been there a couple of times, but I would love to go to Petra. That is on my bucket list. 100%.” Crawford seems to have experienced some sort of experiential shift, post-lockdown. She says she is now finally comfortable not packing her schedule with work and activities or hopping on planes every few days. Instead, she tells me, she is trying to appreciate what this period of reflection has taught her. “I was afraid of being bored. Like, what am I going to do when this is over? Then I thought, actually, I’m pretty good at keeping myself entertained. So, I feel like I came out of that less afraid of not being busy.” Whatever Crawford decides to do next, she won’t be giving up on modeling, something she calls “creating a character,” anytime soon. “I have confidence because I know I’m good at it. But also, you have these connections with people like the hairdresser, the makeup artist, the stylist, the photographer. Sometimes they’re old relationships. So, it’s like visiting with an old friend.”
Jacket, top, skirt jewelry, shoes, Chanel; hosiery, Wolford; hat, Eric Javits. Photo: Thomas Whiteside
She has likened the physical demands placed on a model’s body as similar to those required of athletes. “It’s a skill and something that you get better at. I still enjoy it.” The job doesn’t come without daily maintenance. She tells me she works out at least four times a week and says that her love for bread is very much requited. “It loves me so much that it sticks around. So, I don’t eat a lot of bread.” At 57, it shows: she still fits in the cut-off jeans she wore in the classic 1992 Pepsi commercial.
It’s difficult to imagine that a model of her stature, a woman who literally embodies the aesthetic ideals of beauty, can feel anything other than complete confidence in her appearance. But if speaking to great beauties and celebrities has taught me anything, it is that no one is immune to self-doubt. This is made worse, Crawford says, because of a culture of ageism and the added pressures of scrolling through other people’s (very curated) lives on our phones.
Jacket, skirt, hat, earrings, Moschino. Photo: Thomas Whiteside
“We feel pressure because we’re seeing everyone’s highlights reels, especially on social media,” she says. “I have two sisters that I’m very close to and I have two separate groups of women friends. When I see them, I’m like, wow, your hair looks great, or I love your sweater, or you look amazing. I don’t think we look at ourselves through the same lens, and that, I think, is the work we need to do. To try to look at ourselves with the same love.”
Originally published in the March 2023 issue of Vogue Arabia
Video director: Danielle Gruberger
Style: Patrick Mackie
Fashion director: Amine Jreissati
Makeup: Kate Lee
Hair: Rob Talty
Nails: Yoko Sakakura
Style assistants: Jasmine Morales and Chance Davis
Producer: Sam Allison
On set producer: Helena Martel Seward
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