How Cindy Crawford Invented the Modern Handbook for Professionally Beautiful People

When Cindy Crawford walked into a lounge at the Santa Monica Proper Hotel one morning in June, you could feel her vibe immediately: comfortable, professional, straightforward. No gimmicks. No entourage. Just her veteran publicist Annett Wolf, who gave a brief introduction and disappeared, leaving Crawford at a table displaying an array of products from her Meaningful Beauty skin- and hair-care line, a $400 million brand she launched 20 years ago.

“Where do you want to start?” Crawford asked. “What feels most organic?”

It’s tempting to describe Crawford, 58, as casual, but that’s not quite the case. Dressed in a Celine corduroy jacket, a camisole, Nili Lotan bootleg pants and a Foundrae pendant necklace symbolizing resilience, her beauty is radiant without being overwhelming. A resident of Malibu, where she lives with her husband of 27 years, nightlife and tequila maestro Rande Gerber, she exuded Californian simplicity. She is a familiar face, literally, having been photographed and filmed thousands of times over the course of her more than 35-year career as one of the world’s most successful models.

What felt most organic was starting Cindy’s business. More than the mole above her lip, more than her brown eyes and thick brown hair and healthy physique, Crawford’s interest in transcending modeling to become a brand — decades before personal branding became a career path — is what sets her apart from her peers.

“I always say, ‘I used to model,'” Crawford said. “It’s not, ‘I’m a model. ‘ To me, it’s a verb. It’s not an identity.”

An entrepreneurial model among aspiring supermodels, Crawford invented the modern playbook that today’s generation of professionally beautiful people—including Gigi and Bella Hadid; Hailey Bieber; her own daughter, Kaia Gerber; and much of the Kardashian-Jenner family—follow. Brand partnerships, brand ownership, products, campaigns, deals across multiple forms of media—all center on the self.

“There wasn’t anyone that I thought, ‘I want to have her career,'” Crawford said. “A lot of it was just, ‘Why not?’ or ‘Let’s try this.'”

“Cindy, Inc. Not Just Your Basic $7 Million-a-Year Supermodel”: That was the cover headline of a 1994 Vanity Fair profile that attempted to pinpoint Crawford’s inventive golden touch as a model who could command markets, demographics and products ranging from Vogue to Playboy to MTV to Kay Jewelers. At the time, Crawford was 28, married to Richard Gere (they filed for divorce the following year) and a perfect specimen of exceptional youth and beauty.

Two of the themes of the profile were Crawford’s happiness and the question of whether she would find the “engine” to drive her ambitions. Much was made of her obvious physical appeal, but the article also addressed the fact that Crawford possessed something else—a pragmatism, a lack of pretension and snobbery, a sense of humor and self-awareness—that positioned her for greatness.

“She was born knowing what she was doing,” fashion designer Isaac Mizrahi, one of Crawford’s contemporaries, said in a recent interview. “She’s on her 15th life or something.”

Thirty years later, Crawford has proven herself to be the driver of her own career, a rare example of longevity, graceful aging and business acumen in a superficial world famous for discarding women when the signs of middle age appear.

Crawford has been the face of many brands, perhaps most famously Pepsi. Her hit 1992 Super Bowl commercial is the stuff of advertising legend.

She has been with Omega watches for 29 years. She had a 15-year mega-deal with Revlon that ended when she was 35, at which point she began developing Meaningful Beauty. It is Crawford’s biggest deal, the first equity stake of her career, a 50-50 partnership with Guthy-Renker, the direct-to-consumer subscription marketing company known for brands like Proactiv, JLo Beauty, IT Cosmetics and Tony Robbins Personal Power.

Crawford has never been one to embrace the rarified world of fashion. In a career that has been largely free of scandal, one of her most controversial moves was posing for Playboy in 1988, tastefully photographed by the high-fashion photographer Herb Ritts. A shrewd 22-year-old, Crawford said she thought the Playboy shoot would broaden her audience — straight men, as opposed to the largely female fans of high-end fashion. The broad view with which she approached the opportunity has applied to many of her business decisions.

“My most important collaborations have been with Pepsi and Revlon, not Hermès,” Crawford said. “They’ve been with brands that are for everyone.”

Raised in a working-class family in DeKalb, Illinois, Crawford never lost touch with her roots, even at the height of 1990s glamour, when she starred in George Michael’s “Freedom! ’90” video and was part of Gianni Versace’s inner circle.

“You find yourself in some palazzo in Capri and you think, ‘Wait a minute, I’m just from DeKalb, Illinois,'” Crawford said. “How did I get here and what should I wear?”

Early in her career, her mother visited her in New York and borrowed one of Crawford’s dresses, a simple Donna Karan. “She said, ‘Oh my God, I love this dress. I’m going to buy one exactly like it,’ ” Crawford said. But it cost about $800, she recalled, more than her mother would spend on clothes in a year. Crawford gave her the dress.

“My mom knew quality when she saw it,” Crawford said. “It was an ‘aha’ moment about access and knowledge.”

Mizrahi recalled a photo shoot he did with Crawford in Big Sur, California, in the 1990s. “The crew and everyone, everyone thought she was not smart,” Mizrahi said. “I knew her very well and I was like, ‘What are they talking about? Wait until she opens her mouth.'”

In the late 1980s, before the words “super” and “model” were merged to form a new noun to identify the group of models that included Crawford, Christy Turlington, Naomi Campbell, Linda Evangelista and a few others, she was known as the Midwestern girl who was valedictorian of her high school class and attended Northwestern on scholarship before dropping out to pursue a career in modeling.

She was willing to break the fourth wall and be heard, not just seen — anathema in the fashion world. As the first host of MTV’s behind-the-scenes fashion news program “House of Style,” the beloved show that aired in 1989, Crawford had no broadcasting experience. She was no Elsa Klensch, but she made it look easier than it was.

Turlington recalled that when Crawford left “House of Style,” Evangelista auditioned to host the show. “Linda came in and said, ‘I’m a high-fashion model. I’m going to really show you what it’s like,’” she said. “She didn’t have that sense of humor or lightness.”

Last year, Crawford, Turlington, Evangelista and Campbell reunited on camera for the first time in years for Apple TV+’s “The Super Models.” It was a four-episode trip down memory lane through the supermodels’ heyday — the highs, the lows, the underappreciation, the aging. Campbell and Crawford were the instigators behind bringing the four together for the series, which had been in the works for eight years.

“There’s so much obsession with the ’90s,” Crawford said. “We thought someone would make this documentary. Let’s own our narrative.” All four received executive producer credits. None had final say in the editing.

Crawford was mostly happy with the final product. Her first on-screen moment captures a present-day scene of her on an airplane, vying for a photo that will fetch the highest bid at a charity auction. “I think we all showed exactly who we are,” she said.

Rafael Pavarotti’s cover photoshoot featuring Crawford, Turlington, Campbell and Evangelista that ran in Vogue’s September issue received widespread criticism for over-retouching.

“I don’t think it’s my best Vogue cover ever,” Crawford said. “We have no control over how much they retouch us at Vogue. We don’t even have final approval of the photo. I hated my eyebrows—they over-plucked them. But no one asked me.”

After making a living off her physique for so long, she’s used to the world dissecting her appearance. “I wasn’t interested in changing my face,” she said.

There’s maintenance. She’s had Botox, but less as she’s gotten older because she wants her forehead to match the rest of her face. She also does radiofrequency, microneedling, infrared saunas, cold showers, and a red light mask. She does dry brushing and lymphatic drainage every morning, followed by gua sha with a Meaningful Beauty oil.

“I do those things,” she said. “But in the end, I haven’t really seen anything that’s made such a big difference that I’ve liked about someone.”

“I’m 58,” she said. “Part of me doesn’t want to be doing magazines or photo shoots anymore. If you read the comments, you’ll find some very cruel things. But they’re not worse than what you thought about yourself.”

“But at the same time, am I being complicit in this message to women that we need to hang up our boots at a certain age?”