Cindy Crawford | Let's Extend This Legacy, Shall We?

Via the 25th Anniversary Issue, Under The Silver Moon!

Photographed by

Greg Swales

Styled by

Mui-Hai Chu

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BOTTEGA VENETA jacket, shirt, pants, tie, and shoes.

If someone were to put together a time capsule recapitulating the past 25 years of American culture, surely a photo of Cindy Crawford would be inside. Maybe it would be a frame of the Pepsi commercial, (in which no one has sported a better blowout since), maybe it would be her Playboy cover, or perhaps one of the thousands of magazine clips, video snippets worshiping her walk, her red carpet appearances, or her chic off-duty looks (Crawford notes in our conversation that her favorite late-90s fashion trend is and always will be jeans and a leather motorcycle jacket).

Crawford, a girl whose first few jobs were working in the cornfields and babysitting in her small hometown of DeKalb, Illinois, is a rare icon that represents the past, the present, and the future. Her, Naomi Campbell, Christy Turlington, and Linda Evangelista forged a new path for American models. Labeled “The Big Four,” they transformed the job of modeling, what was once at best a three-year career, into something that could create cultural icons, a status Crawford has held for the past 40 years. Apple TV recently released a docuseries on the quartet and their impact, The Supermodels, recounting the steps that led to their stardom. Representing brands, appearing in music videos, and making headlines for walking a certain runway all seem to be perfectly normal ways of the modeling world today, but it began in the 90s, and Crawford was doing it first.

BALENCIAGA dress and skirt and TIFFANY & CO. necklace.

Today, she creates a new understanding of how a woman can take command over her own career, which Crawford has been doing since she was in her late teens modeling in Chicago at 16, even before hitting the New York fashion scene that would embed her into the zeitgeist for basically her entire life. And, of course, she single-handedly has an impact on the future of modeling. In a literal sense being the mother to Kaia Gerber, who’s made the high-fashion couture rounds and is now starring in films–and in a figurative sense, in that there are likely few models working today whose careers have not been somewhat defined by what Crawford’s was, and is. She’s also mother to Presley Gerber, who takes inspiration from both his parents having worked as a model and investor. Her husband, Rande Gerber, is co-founder of the beloved Casamigos, a tequila company that Crawford lent her hand and stardom to help build the brand into the billion-dollar behemoth it is today.

BALENCIAGA dress and skirt and TIFFANY & CO. necklace.

It might seem that Crawford is the kind of person who stumbles upon luck, success after success. A MTV show here, a brand ambassadorship there, entrepreneurship after lunch–but she possesses the kind of charm that makes her hard work look easy. She doesn’t complain, and she keeps it moving. She knows herself and she trusts her intuition; after all, you don’t make it several decades at the top on the outs with yourself, and you can’t navigate this billion-dollar industry without being both sweet and savvy.

In celebration of FLAUNT’s 25th Anniversary and in appreciation of Cindy and her cultural contributions, we speak with her about life and legacy.

BALENCIAGA dress and skirt and TIFFANY & CO. necklace.

So much has changed about the fashion industry, media, and culture since you began your work as a model. How did you and do you adapt to an ever-changing business? What about the modeling industry’s past do you miss? And what’s better off staying in the past?

The truth of the matter is that the actual job of modeling, that is being in front of a camera to showcase clothes or cosmetics or whatever it is, hasn’t changed that much. The biggest change in that area was the switch to digital cameras which started happening in the late 1990s and early 2000s. The advantage to that was that everyone could see in real-time the images that were being captured instead of relying on a Polaroid. The negative was that it took away some of the magic and sometimes there were too many voices chiming in rather than really just the photographer’s eye. The other big changes are more around the never-ending need for digital content and behind-the-scenes. It makes for more work for everyone on set but at the same time, allows models and everyone else to have a say in how they present themselves to their fans.

MIU MIU jacket and top, DET BLEV SENT skirt, GIVENCHY sunglasses, and TIFFANY & CO. necklace.

You’ve taken certain risks in your career that have launched you further into success. What kind of advice do you have on taking risks? What was the last risk you took?

I have taken a lot of risks as a model, and I’m not actually sure where I got the bravery from! I think the biggest were one, posing for Playboy which eventually was one of the reasons I was asked to host MTV’s House of Style. The second was deciding not to renew my contract with Revlon at age 35 after 17 years of working as their spokesperson. I intuitively knew that if I were ever going to do my own thing, that was the time. Shortly after, I started my skincare line, Meaningful Beauty. We are celebrating our 20th anniversary next year! The last risk I took was doing a parody of my iconic Pepsi commercial for a risqué song called “One Margarita” with That Chick Angel. I knew some of my followers would be surprised because the song is raunchy, but I also thought it was hilarious and it was fun to poke fun at myself.

PRADA top, skirt, and shoes, and PRADA FINE JEWELRY necklace, bracelet, and ring.

What has been your experience of sharing a passion with your daughter? As a mother, how do you toe the line between mentorship and allowing Kaia to forge her own path? Were there any special ‘rite of passage’ moments you recall?

One of the unexpected things about Kaia now being in fashion is that it has given us the opportunity to work together and to see each than just mother and daughter. Definitely, in the beginning, I was Kaia’s “momager.” But as she has found her own way, I have stepped back and have really allowed her to make her own decisions. I try not to give my opinion unless she asks for it.

TORY BURCH dress, BALENCIAGA  boots, AKILA sunglasses, PRADA FINE JEWELRY necklace, and OMEGA watch.

Can you tell us about the genesis of Meaningful Beauty, and what drew you to entrepreneurship? What are some mistakes that you’re glad you made? What have you learned about yourself in this process?

When I decided to do my own “thing,” skincare was the obvious choice because taking care of myself and my skin was something that I was passionate about. Showing up on set with great skin was part of the job as a model. I also wanted to share all the information and treatments that I had gotten from Dr. Sebagh. In the beginning, I think I was very controlling. As I started to work more with my team, I was able to trust them more to do what they are good at and let me do what I am good at. I’ve learned that I care deeply about empowering women and helping them find ways to lead their best lives—even if it’s as simple as feeling confident in your skin.

VALENTINO shirt and shoes, LEVI’S x DENIM TEARS jeans, B.B. SIMON belt, TIFFANY & CO. necklace, and OMEGA watch.

Mental health has been an emerging conversation in recent years–how do you resonate with the topic?

I love that people are more comfortable talking about mental health. I don’t know why our culture has historically told us we all have to hide our fears and insecurities. I know for me, that when I am open about my troubles or worries, not only do I get the comfort and understanding that I need, but it also opens the door for others to share. Community is so healing.

LOEWE top and pants, MIU MIU shoes, and talent’s own ring.

How do you relate to the phrase, ‘every cloud has a silver lining’?

I do think there is truth in that phrase although often it is hard to see in the moment. So much of it is about mindset. I think I like the idea of choosing to see the glass as half full—trying to see the good in everyone and every situation.

LOEWE top and pants, MIU MIU shoes, and talent’s own ring.

What advice would you offer your 15-year-old self?

If I could go back, I think I would tell my 15-year-old self to not take things quite as seriously. I think I missed out on some opportunities because I was afraid I didn’t belong—I call it the Emperor’s New Clothes syndrome.

LOEWE suit, VALENTINO shirt, ROGER VIVIER shoes, and TIFFANY & CO. necklace.

So much of your business is communicating through a camera. What’s something about you that can’t be captured in a photo?

I don’t think a camera can capture how much I try to be a good wife, mother, daughter, sister, and friend.

MIU MIU top, TIFFANY & CO. earrings, and OMEGA watch.

Have any books or films moved you recently?

I am really into audiobooks. Two of the last ones I listened to were Mad Honey by Jodi Picoult and Jennifer Finney Boylan, and as for non-fiction, The End of the World is Just the Beginning by Peter Zeihan.

MIU MIU top, TIFFANY & CO. earrings, and OMEGA watch.

What do you love about magazines?

There is something about flipping through the pages of a glossy magazine that isn’t like anything else. It’s the anticipation and discovery on every page. The gorgeous images that are immortalized as well as an article that you might not even know you were interested in.

You’ve shared your image, your life, and your legacy with the public sphere. What do you hope to be remembered for?

I hope my children remember being unconditionally loved by me. 

BALENCIAGA jacket, shorts, and boots and stylist’s own bra.

Photographed by Greg Swales at AGPNYC

Styled by Mui-Hai Chu

Written by Franchesca Baratta

Hair: Dimitris Giannetos at Opus Beauty

Makeup: Harold James at The Wall Group

Nails: Stephanie Stone at Forward Artists

Production: Alexey Galetskiy at AGPNYC 

Flaunt Film: Chevy Tyler

Digi Tech: Dan Brittain

Set Designer: Lucy Holt

Set Design Team: Liam Burke, Dillan Sammons

1st AC: Casey van der Touw-Sandretto

Sound Mixer: Andrés Acosta

Editor and Sound Design: Leila Lorenz

Styling Assistants: David Gomez, Justice Jackson, and Erin Zhang 

Photo Team: Yolanda Leaney, Juliet Lambert, Sandy Rivas, Michael Camacho

Production Team: Ivan Shentalinsky

Location: Stone Fox Ranch

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No items found.
Cindy Crawford, Flaunt Magazine, Issue 190, The 25th Anniversary Issue, Under The Silver Moon, Franchesca Baratta, Mui-Hai Chu, Greg Swales, Bottega Veneta, Prada, Prada Fine Jewelry, Omega Watches, Miu Miu, Balenciaga, Levis, B.B. Simon, Loewe, Tory Burch, Valentino, Tiffany & Co., Meaningful Beauty