Cindy Crawford is focused on transitions. Almost 30 years ago, she reinvented what a model’s career could become when she embarked on a spree of entrepreneurial ventures, including fronting a Pepsi campaign and hosting MTV’s House of Style. She followed that with a landmark fitness video and later, a successful furniture line. In today’s cultural landscape, it is a truism that a successful cover girl can become a mogul, but when Crawford blazed the trail, it was unthinkable. Today, she’s still committed to forging new paths. After turning 50 last year, and seeing her 15-year-old daughter, Kaia Gerber, named a fresh face in fashion, the supermodel is scanning the horizon for another new direction.
“For me it was really hard; the idea of turning 50 was daunting. For so long I was the 20-year-old model on the cover of Vogue, or 25 or 30—and then all of a sudden my daughter is becoming that,” says Crawford. “My mother was here for Mother’s Day and I was talking to her about how I change the narrative for who I am at this age. I don’t want to spend my fifties trying to get back to where I was in my thirties. Even though, yes, maybe I would like my skin or my waistline to be the same, I’ve worked hard and evolved into this person.”
Her first evolution began in 1992 when Crawford, unofficially christened the ideal of American beauty after gracing more than 200 fashion magazine covers, embarked on series of fitness videos with her trainer, Radu Teodorescu. The project was a success and had her thinking about what to do next. Crawford displayed an aptitude for choosing projects that, while seeming like gambles at the time, ended up propelling her career to the next level. Knowing how to make those decisions was not easy at first, as modeling is (for the successful, at least) a fairly paint-by-numbers endeavor. “Pretty much, your agent just picks up the phone, then people call you and say, do you want to work for Versace? Yes. Or do I want to work with Revlon? Yes,” she explains. Taking bigger chances—like signing on for House of Style or appearing in Playboy, two big risks that ended up paying off handsomely—was another matter.
“For so long I kept thinking, I just want a business daddy—I kept looking for that person who was going to tell me, ‘You should do this,’ and, ‘You should do that,’” she says. “And then I realized I have to be my own business daddy, because no one knows my brand better than I do. When I started trusting that, I think it just got easier.” The results were projects, whether in fitness, style or home interiors, which feel organically Cindy.
One of the more remarkable things about Crawford is her refusal to stop moving and growing. Last fall she enrolled in a three-day financial boot camp for women at UCLA. The valedictorian of her Illinois high school who left college when fashion beckoned, Crawford wanted to become more comfortable asking the important questions in business meetings. “I loved being in the classroom again,” she says. “It was especially nice to do it with other women. You don’t want to be embarrassed, asking a stupid question, but I think we all felt we were in a safe enough environment.”
Another benchmark of success, Crawford has been happily married to Rande Gerber for almost 20 years. An entrepreneur in his own right, Gerber has successfully owned and operated nightlife and hospitality businesses since he graduated from college. He might even be on the cusp of his greatest success to date, along with business partners George Clooney and real-estate developer Mike Meldman, in creating a much raved about tequila company Casamigos.
The most recent business initiative for Crawford is her skincare brand, Meaningful Beauty. She recently traveled to Florida to shoot her two grandmothers—one aged 98, the other 94—for the line. “My 98-year-old grandmother is still giving her hairdresser a hard time because she has a very particular way that she likes her bangs cut,” Crawford explains. I was asking her, why does beauty still matter at this point?” And she said, ‘I feel better, I have more confidence.’ That’s a cue for all of us.”
That confidence is apparent in the next generation of the lineage. Her son, Presley, 17, has a Calvin Klein campaign under his belt, and Kaia is the face of Marc Jacobs Beauty. “It’s certainly not something I encouraged, nor did I discourage it. I think what I’m realizing, especially now that they’re graduating from high school, is a lot of kids end up doing what their parents do,” she says. “The fact they were interested in fashion shouldn’t be totally surprising. And because they’re my kids, they have an easy point of entry.”
Crawford, who attended Northwestern University on a chemical engineering scholarship, is also well aware that one’s teenage pursuits don’t necessarily foretell a lifelong career. “For my son, I think he’s more in it for the travel—for guys it’s different, it’s a nice finishing school for him,” she says. “For my daughter, she’s seen what an amazing career I’ve had, and how hard I work and how seriously I take it. But she’s only 15, so we’ll see what happens.”
The fashion world her children inhabit is one that has changed greatly since Crawford first broke onto the scene in 1986 with a Richard Avedon Vogue cover. For someone whose name is virtually synonymous with the feminine ideal, she sees beauty as something that is much less narrowly defined than it was in the ’90s glamazon era. “Because of social media, you see that beauty isn’t rare. Beauty is everywhere we look—I think that’s very empowering for women,” she says. “Before we only had a handful of women who were appearing in magazines. Now you can go on Instagram and someone you’ve never heard of, who maybe only has one follower or maybe has nine million—you see they’re beautiful. Sometimes it’s the filter, but I think women are emerging through. I’m no stranger to filters, but women can recognize their own beauty.”