How Cindy Crawford Invented the Modern Playbook by Which the Current Generation of Models Flourish

When Cindy Crawford walked into a lounge in the Santa Monica Proper Hotel on a morning in early June, her vibe was immediate: comfortable, professional, direct. No artifice. No entourage. Just her longtime publicist Annett Wolf, who made a brief introduction and disappeared, leaving Ms. Crawford at the head of a table set with a display of the products from her Meaningful Beauty line of skin and hair care, a $400 million brand she introduced 20 years ago.

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

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

What felt most organic was to start with the business of Cindy. More than the mole above her lip, more than her brown eyes and va-va-voom hair and her healthy physique, Ms. Crawford’s interest in transcending modeling to become a brand — decades before personal branding was a career path — is what has distinguished her from her peers.

“I always say, ‘I modeled,’” Ms. Crawford said. “It’s not, ‘I am a model.’ It’s a verb to me. It’s not an identity.”

An entrepreneurial role model among aspiring supermodels, Ms. Crawford invented the modern playbook by which the current generation of professionally beautiful people, including Gigi and Bella Hadid, Hailey Bieber, Ms. Crawford’s own daughter, Kaia Gerber, and most of the Kardashian-Jenner family, abide. Brand partnerships, brand ownership, products, campaigns, deals across various forms of media.

“There wasn’t someone that I was, like, ‘I want her career,’” Ms. Crawford said. “A lot of it was just, like, ‘Why not?’ or ‘Let’s try this.’”

“Cindy, Inc. Not just your basic $7-million-a-year supermodel.” That was the cover line of a 1994 Vanity Fair profile that tried to put a finger on Ms. Crawford’s newfangled golden touch as a model who could command markets, demographics and products that ranged from Vogue to Playboy to MTV to Kay Jewelers. At the time, Ms. Crawford was 28, married to Richard Gere (they filed for divorce the following year) and a perfect specimen of youth and exceptional beauty.

Two of the profile’s themes were Ms. Crawford’s happiness and the question of whether she would find the “engine” to power her ambitions. Much was made of her obvious physical appeal, but the article also addressed the fact that Ms. 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,” the fashion designer Isaac Mizrahi, one of Ms. Crawford’s contemporaries, said in a recent interview. “This is her 15th life or something.”

Thirty years later, Ms. Crawford turned out to be the driver of her own career, a rare example of longevity in an industry famous for discarding women once a whiff of middle age enters the picture.

Ms. Crawford has been the face of many brands, perhaps most famously Pepsi. Her blockbuster 1992 Super Bowl ad is advertising legend. She has been with Omega watches for 29 years. She had a 15-year mega-contract with Revlon that ended when she was 35, at which point she started developing Meaningful Beauty. It is Ms. Crawford’s biggest business, the first ownership stake of her career, a 50-50 partnership with Guthy-Renker, the direct-to-consumer subscription marketing firm known for brands like Proactiv, JLo Beauty, IT Cosmetics and Tony Robbins Personal Power.

Traditionally an infomercial model, the Guthy-Renker way is not sexy. “You could say that infomercials were below Cindy,” said Greg Renker, who founded the company with Bill Guthy. “She knew it. She reminded us of it.”

Mr. Guthy and Mr. Renker pursued Ms. Crawford for years before she took them seriously, demanding equity partnership.

If Ms. Crawford was going to do an infomercial skin-care line, it was going to be her way. She wanted to develop the products with Dr. Jean-Louis Sebagh as a distillation of the antioxidant treatment he provides in his Paris practice, but made more accessible.

“I was, like, ‘Pretty much every director you’ve used, I don’t want to use,” she said. “‘I have to do it totally different.’”

Mr. Renker said Meaningful Beauty was Guthy-Renker’s biggest investment at the time. Their bet on Ms. Crawford did not pay off at first.

“It was difficult to present Cindy warmly, even though she was in fact a warm and terrific person,” Mr. Renker said. “At that time in supermodeldom, they were all kind of intimidating and untouchable. We almost quit.”

They recalibrated, emphasizing the connection to Dr. Sebagh and filming the infomercials with Ms. Crawford speaking to a peer, rather than directly to the customer. The brand flourished, and it no longer relies solely on television infomercials or Ms. Crawford. Customers buy the products through the brand’s website, social media and from wholesale outlets like Amazon, and the line has additional spokeswomen, including Ellen Pompeo and Porsha Williams.

“I didn’t even want my name on the brand,” Ms. Crawford said. “I hoped that it would have a life bigger than just me.”

Ms. Crawford has never clung to the rarefied world of fashion. In a career unmarked by scandal, one of her most controversial moves was doing Playboy in 1988, tastefully shot by the high-fashion photographer Herb Ritts. Preternaturally savvy at age 22, Ms. Crawford has said she thought the Playboy shootwould increase her audience — heterosexual men, as opposed to the primarily female fans of luxury fashion. The wide lens through which she viewed the opportunity has applied to many of her business decisions.

“My most important collaborations were with Pepsi and Revlon, not Hermès,” Ms. Crawford said. “They were with brands that are for everybody.”

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

“You find yourself at some palazzo in Capri, and you’re, like, ‘Wait, I’m just from DeKalb, Illinois,’” Ms. Crawford said. “‘How did I end up here, and what am I supposed to wear?’”

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

“My mom recognized quality when she had it,” Ms. Crawford said. “It was an ‘aha’ moment that was about access and knowledge.”

Mr. Mizrahi recalled a shoot he did with Ms. Crawford in Big Sur, Calif., in the ’90s. “The crew and everybody, they just assumed that she was not smart,” Mr. Mizrahi said. “I knew her extremely 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 band of models that included Ms. Crawford, Christy Turlington, Naomi Campbell, Linda Evangelista and a handful of others, Ms. Crawford was known as the small-town Midwestern girl who was co-valedictorian of her high school class and attended Northwestern on scholarship before dropping out to pursue modeling.

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

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

Last year Ms. Crawford, Ms. Turlington, Ms. Evangelista and Ms. Campbell were all on camera together for the first time in years for the Apple TV+ series “The Super Models.” It was a four-episode trip down memory lane through the headiest of supermodel times — the ups, the downs, the underestimation, the aging. Ms. Campbell and Ms. Crawford were the instigators behind getting the foursome together for the series, which was in the works for eight years.

“There is so much obsession with the ’90s,” Ms. Crawford said. “We’re, like, someone is going to do this documentary. Let’s own our own narrative.” All four women received executive producer credits. None had final cut.

Ms. Crawford was mostly happy with the finished product. Her first present-day on-screen moment captures her on a plane, jockeying for a photo that will fetch the highest bid at a charity auction. “I think we all came off as exactly who we are,” she said.

The cover shoot by Rafael Pavarotti featuring Ms. Crawford, Ms. Turlington, Ms. Campbell and Ms. Evangelista that ran in the September issue of Vogue received a fair amount of backlash for gratuitous retouching.

“Do I think it’s my best Vogue cover ever? No,” Ms. Crawford said. “We don’t have say on how much they retouch us with Vogue. We don’t even have final approval of the picture. I hated my eyebrows — they way overdrew them. But no one is asking me.”

After making a living on her physique for this long, she’s used to the world dissecting her looks.

“I was not interested in changing my face,” she said.

There is upkeep. She has done Botox, but less as she gets older because she wants her forehead to match the rest of her face. Radio frequency, microneedling, infrared sauna, cold plunge, a red light mask. She does dry brushing and lymphatic drainage on herself every morning, followed by gua sha with a Meaningful Beauty oil.

“I’ll do those kinds of things,” she said. “But in the end, I truly haven’t seen anything that’s made such a huge difference that I like on anyone.”

“I’m 58,” she said. “Part of me would want to not be doing magazines or photo shoots. If you want to scroll through your comments, you will find really mean things. But they’re not meaner than you’ve thought about yourself.” “But at the same time, am I being complicit in this message to women that we need to hang it up at a certain age?”