Cover story

Incredible Woman

With

Cindy Crawford

At 60, CINDY CRAWFORD remains one of the most monumental models of her era. Here, the iconic supermodel, businesswoman and reluctant trailblazer talks to KASIA HASTINGS about her extraordinary career, posing for Playboy, working with daughter Kaia Gerber, and why she can’t wait to be a grandmother

Photography Yulia GorbachenkoStyling Charlotte Blazeby
Cover Stories
This image: coat, Carolina Herrera. Opening image: coat, Carolina Herrera; sunglasses, Thistles; gloves, Agnelle

It’s 8am in Ontario, Canada, and Cindy Crawford is perfectly on time. She greets me from Gerber Point Lodge on Lake Joseph, her family’s off-grid oasis, where she, her husband of 28 years, Rande, and their two children, Kaia and Presley, have been spending summers for the past 22 years. “It’s a very unplugged place. We’ll work out on our dock, go in our sauna, jump in the lake, go on the boat and have what we call docktails – like a cocktail party but on the dock,” she tells me with a sated end-of-vacation smile. I ask what exactly a docktail party entails and she assures me it’s nothing more than charcuterie plates and cocktails, maybe a game of backgammon if things get really wild.

Crawford looks impeccably put together in a very effortless way. Appearing on screen on the dot of 08.00 hours, her signature mane of chestnut-brown hair hangs elegantly over a light-green sweatshirt that she has accessorized with day diamonds and a coffee cup decorated with the American flag. We aren’t here just to talk about her famously good timekeeping, although it is something she’s built her reputation on, a brand on. As well as being a – if not the – ’90s supermodel, of course. And then there’s her latest chapter as the famous mother of model, actor and Gen Z muse Kaia Gerber, Crawford’s 25-year-old daughter who now holds her own place at fashion’s top table.

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“At times I’ve been TEMPTED to step back more, but I don’t want to add to that idea that WOMEN of a certain AGE need to be more invisible”

Since signing with her first agency IMG at 13, Kaia has worked with all the major houses, walked shows as soon as she could at 16, and secured her own September cover moment this month, alongside Homer Gere, to celebrate her leading role in new Disney series The Shards. For many of us, it’s become impossible to talk about Cindy without mentioning Kaia, from the similarities in their looks to the will to label Kaia’s excellent style choices ‘Cindy-inspired’. While both talents in their own right, the mother and daughter have become inextricably linked in the public consciousness. I suggest that the constant comparisons must become a little irritating at times: “It doesn’t annoy me at all. I love it, but I don’t know what it’s like to have a famous parent,” she laughs. “I think for Kaia, it’s just part of who she is, and she’s going to have to handle it. There are perks that come with it, and then there are probably annoying things, and I have acknowledged that with her. I’m sure, at times, it sucks.”

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Jacket, skirt, pumps, and tights, Valentino Garavani
Blazer, pants, T-shirt, and loafers, The Row

Crawford recognizes that there have been plenty of upsides for them both. “We’ve had these special moments that, if I wasn’t in fashion, we wouldn’t have had. Like when we were both in the Versace show in 2017. I wasn’t there as Kaia’s mom, and she wasn’t there as my daughter. She was there, I was there, both for our own reasons, and there’ve been a few of those little moments. I love whenever I get to work with Kaia. It’s really fun.” Beyond their obvious physical similarities – cascading brunette hair, sharply defined cheekbones, dark expressive eyes and all-American smiles – the most comparable trait Kaia shares with her mother is her renowned work ethic, which has no doubt contributed to her own success in the industry.

“The FIRST time I did Playboy, I said, ‘I don’t want MONEY. I want CONTROL’”

Crawford is, and has always been, the utmost professional. Whatever string to her illustrious bow she is pulling, she does it with precision, never missing her target, always delivering and always on time. We know her as an incredible model, mother, entrepreneur and wife, a self-made woman from the Midwest who, now at 60, has been working pretty much continuously for five out of her six decades. Is she thinking about stopping anytime soon? “At times I’ve been tempted to step back more, but I don’t want to add to that idea that women of a certain age need to be more invisible. Even though there are days when I feel like, ‘Oh, why did I say yes to the shoot?’ – or maybe, ‘It’s time’.” The question of retirement follows her like it does so many icons, but she is typically pragmatic on the subject: “Modeling really is a skill that you get better at. It’s probably like a football player or a soccer player having to choose when they want to retire. You’re like… but I still like it.”

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    Dome gold-tone earrings
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    Blake mini leather shoulder bag
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Dress, and tights, Gucci
Shirt, skirt, gloves, pumps, and tights, Tom Ford

“As MUCH as I defer to other people about some things, I am the world EXPERT on Cindy Crawford… Learning to use my VOICE with authority was part of my maturing as a businesswoman”

It certainly doesn’t feel like ‘it’s time’ for Crawford just yet. She has carved a career out of taking chances other models might have been afraid to take, from doing Playboy and her MTV show House of Style to starring in the 1995 thriller Fair Game and, most recently, walking in the Gucci Cruise show in New York’s Times Square. Talk of her two Playboy spreads shot by legendary photographer Herb Ritts (in 1988 and 1998) still brings a small but defiant smile to her face. “The first time I did Playboy, I said, ‘I don’t want money. I want control’. I had approval of the pictures. I even had approval to kill the story if I didn’t like it,” she says before pausing for a moment to gather her thoughts. “Maybe some people would still question that decision, even though we were shooting for Vogue at the same time, and you couldn’t tell what was for what because for French Vogue you could do topless. So, I think I stand by that decision, and because of that, I got MTV and things like Pepsi that were more appealing to men and women, and not just fashion.”

I attempt to call her a trailblazer and she’s quick to bat the compliment away. “I think in some ways I get more credit than I deserve, because it wasn’t like I had this master plan. But what I did do is I took chances, and you know, if there wasn’t a good reason to say no, I was like, ‘Let’s try’.” It’s a strategy that has served her well and one that has delivered iconic moments. Be it playing her part in George Michael’s Freedom! ’90 video (and the subsequent supermodel lip sync to the track at the finale of Gianni Versace’s fall/winter 1991 show) or dressed as George Washington on the inaugural cover of JFK Jr.’s George Magazine in 1995, Crawford’s willingness to say yes has certainly paid off.

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Blazer, pants, shirt, tie, and shoes, Dolce&Gabbana
Sunglasses, Celine Eyewear

Her latest roll of the dice saw her create another iconic Crawford fashion moment with Gucci creative director Demna for the house’s aforementioned Cruise 2027 takeover of Times Square in May. Surrounded by its famous neon lights and giant screens, she closed the show in a dramatic feathered black strapless gown.“The dress was so heavy and my heel came out of my shoe right when I walked out and I never got it back in. But that dress was so big you couldn’t see it. I was like, ‘Just don’t lose the shoe. Just keep the shoe on. I don’t want to be like Cinderella’.” Naturally, no one noticed this minor wardrobe malfunction, such is Crawford’s unparalleled professionalism. Her return to the runway wasn’t without reservation, but support from a fellow model was on hand. “Kaia was very supportive and proud of me for doing it because she knew I was like, ‘Wait, is this a good idea or a bad idea?’ and it was such a big show.” From a pre-show lunch to the afterparty, Crawford’s daughter was by her side, just as Crawford had been for Kaia in her early modeling days. “I think seeing me do something that I had some nerves about is good for her to see.”

‘Cindy Crawford’ the brand might appear a paragon of perfection now, but for Crawford, it’s always been as much about taking risks and allowing yourself to fail as it is about hitting the target. A gamble that perhaps didn’t pay off professionally was her feature film debut, Fair Game. In it, Crawford plays Kate McQueen, a lawyer whose life becomes endangered when she discovers something she shouldn’t have. Enter William Baldwin, the police detective assigned to protect her, who she inevitably falls in love with. “You know, in retrospect, maybe I would have taken acting classes before I did it, but I’m proud of myself for doing it,” she says smiling. But for Crawford it offered an important lesson: “I realized that I’m only comfortable as myself in front of the camera. It was actually such a gift because I was able to let that [part of my career] go.”

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Jacket, Valentino Garavani

Another decision that attracted some unwanted headlines was a 1993 Vanity Fair cover shoot starring queer Canadian singer-songwriter k.d. lang, shot again by Herb Ritts. Crawford recalls the photographer ringing her up the night before and asking her to be “an accessory or a prop” in lang’s playful exploration of gender stereotypes: “I totally trusted her, beloved k.d. lang.” Titled ‘k.d. lang Cuts It Close’, the shoot saw lang dressed as cliché of a man in a vest, shirt and tie, sitting in a barber’s chair complete with a neck covered in shaving foam, with Crawford straddled over her wearing nothing more than a black swimsuit and a pair of lace-up boots. “Afterwards, it was interesting because, let’s say that would have been a male pop star or singer, and I had done the exact same everything. People would not have thought, ‘Oh, they’re having a relationship’ or that she’s making a statement. But because it was more titillating, because it was two women, I think it became more of a story.”

“My LIFE has given me so much access and I grew up in a place where I didn’t have ACCESS, so I kind of see myself as a liaison between this high-fashion world and the GIRL that I was”

Thankfully, the story today has moved on a lot since the ’90s, but in many ways women continue to face similar challenges. Crawford reflects on her own position as an entrepreneur, having celebrated 22 years of her beauty brand, Meaningful Beauty, this May. “As much as I defer to other people about some things, I am the world expert on Cindy Crawford,” she says knowingly. “I think women do this a lot, and maybe men too, but we give our power away. Learning to use my voice with authority was part of my maturing as a businesswoman.” From the early infomercial days to competing with the major French players, alongside cosmetic specialist Dr. Jean-Louis Sebagh, Crawford has built a solution-based beauty brand with a global following. Her mission? To share some of the beauty secrets she has been fortunate enough to uncover during her career. “My life has given me so much access and I grew up in a place where I didn’t have access, so I kind of see myself as a liaison between this high-fashion world and the girl that I was.”

Crawford talks passionately about the women in her life. Of the many women she holds in high esteem – her daughter, her two sisters, the groups of friends that she plays mahjong with in LA, Miami and now Ontario – it’s her mother that she admires the most. “I think the biggest reason I admire her is she is a bit of a Pollyanna,” she says. (A Pollyanna refers to a person who is overly optimistic, always cheerful and positive.) “I used to not respect that. I used to think she doesn’t get it. Like, why isn’t she mad at this person? And I realize it’s not that she doesn’t get it. It’s a choice. She chooses to see the glass half full, and she had a lot of reasons not to. We lost my brother; she got divorced; we grew up, I wouldn’t say poor, poor, but pretty, you know… Like sometimes we didn’t have money for milk until my dad got his paycheck. My mother was never bitter. And I think, wow, that took so much strength.”

Jacket, skirt, pumps, and tights, Valentino Garavani
Blazer, pants, and loafers, The Row

She also credits her mom with informing her own approach to parenting her adult children. “My mother’s also a great mother because she’s pretty good at not giving advice unless you ask for it. I’ve realized that’s really hard to do, but now that my kids are older, I do try to.” With both Kaia and Presley making their own way in the world, Crawford and Rande have had to learn to sit back. “When they become adults, all of a sudden you’re like, okay, I’ve got to back off here. It might not be the way I would do it, but you know…” she concedes. Like so many parents who build their lives around their families, there has also had to be an adjustment in terms of her marriage. “When you get married, you talk about what kind of family you want or where we’re going to live. But no one ever talks about what this phase looks like, empty nesting, because it’s so far away you can’t even imagine it. But it’s an opportunity for us to redefine our relationship. What do we want to do, do we want to travel, do we not want to travel? We haven’t answered those questions yet but we’re asking the questions and it’s fun trying to figure that out together.”

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“One thing I really am looking FORWARD to is being a grandmother. I do HOPE I get to experience that, because it looks REALLY fun”

There is plenty still keeping Crawford busy; her career, alongside Naomi Campbell perhaps, the most enduring of all the Supers. “I’ve already done so much. I couldn’t have dreamed of my career, right? I would have set the bar much lower,” she says, laughing. “One thing I really am looking forward to is being a grandmother. I’m at the age where a lot of my friends are starting to have grandkids, and even though I don’t think either one of my kids is close, I do hope I get to experience that, because it looks really fun.”

As we say goodbye, at precisely 08.59, I thank her and tell her how thrilled we are with the shoot, to which she replies, “I mean, I do shoots, but it’s PORTER, so it’s definitely Fashion with a capital F.”