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A Timeless Beauty: Cindy Crawford's Journey Through the Decades

She may be one of the original supermodels, yet despite often being defined ‘ageless’, Cindy Crawford, who features on outgoing British Vogue Editor Edward Enninful's final front cover, has never been one to shy away from the realities of getting older.

Naomi Chadderton
Naomi Chadderton
An experienced editor and journalist specialising in news and lifestyle.

Cindy Crawford has always had a refreshing take on ageing. By the time she approached her fifties, she’d started noticing her age in little things: “Your skin, your hair, your body. I take care of myself but I know that I’m a 51-year-old woman,” she told The Cut at the time.

In the realm of supermodels, few names shine as brightly as Crawford, who features in the 40 Vogue icons gracing the cover of March's issue – the final edited by outgoing British editor Edward Enninful. From her humble beginnings in the small town of DeKalb, Illinois, to gracing the covers of countless magazines and dominating the fashion runways of the ‘80s and ‘90s, there’s no doubt she has cemented her status as a true icon of beauty and success, and what a journey it has been. Impressive stuff.

A Supermodel in the Making

Born on February 20 1966, Cynthia Ann Crawford grew up with dreams bigger than her small-town surroundings. With her signature mole above her lip and captivatingly statuesque figure, she was catapulted into the industry when she was scouted by a local newspaper photographer at the age of 16, and little did she know that this encounter would be the catalyst for her meteoric rise to fame.

It wasn’t long until she had signed with the legendary Elite Model Management and moved to New York City, where her classic American beauty and unparalleled presence quickly caught the attention of the fashion world. She soon became a muse for renowned photographers like Richard Avedon and Herb Ritts, gracing the covers of Vogue, Elle and Harper's Bazaar.

Crawford's career went on to reach new heights in the ‘90s, and she became synonymous with luxury brands like Versace and Chanel, walking the runways of Paris, Milan and New York with effortless grace. It’s no surprise that to this day, alongside Naomi Campbell, Linda Evangelista, Christy Turlington and Claudia Schiffer, she will always be known as one of the big five original supermodels.

“I’m not 25, so why should I be trying to look 25? Why do I want someone to mistake me for a 25-year-old? I’ve had children. I have all this life experience.”
Cindy Crawford at a movie premier in 1997.

A Legend of the Ages

In 2000, exactly 10 years since her career had skyrocketed, Crawford quit full-time modelling at the age of 34. Not that she’s slowed down since then – not only has she written a book, Becoming, worked as a spokesperson for several brands and even launched her furniture line, she’s also an advocate for a number of charitable causes including childhood leukaemia research (her brother Jeffery died from the disease at age three) and women's empowerment initiatives.

In 2021, at the age of 55, she even recreated her iconic 1992 Pepsi advert to raise money for a children’s hospital in Madison, Wisconsin, returning to the original location of the advert nearly three decades later to pose in the same outfit – a white tank top, blue denim cut-off shorts and red stilettos. If anything, she looked even better than the first time around.

Cindy Crawford, Rande Gerber and their children Presley Walker Gerber and Kaia Gerber at a Los Angeles premier in 2016.
“No matter what I do, I’m not going to look 20, or 30. I just want to look great for 50. There’s pressure on women to do the undoable, which is not age. But it’s about looking great for however old you are, regardless of what that number is.”

Cindy Crawford: Ageing with Grace

Unsurprisingly, people tend to hold models to unrealistic beauty standards, especially as they get older, but Crawford proudly rejects any age expectations people might have for her and has shared plenty of words of wisdom with everyone who’s afraid of ageing.

In interviews, Crawford has emphasised the importance of self-acceptance and self-care at every stage of life. She also advocates for a holistic approach to beauty that prioritises inner confidence and well-being over external appearances, believing that true beauty comes from living authentically and embracing one's imperfections.

That doesn’t mean she hasn’t had a hard time with people online reacting to her changing appearance, saying: “I don’t need everyone on Instagram pointing out that I don’t look the same way I did when I was 20. I know that. But after the struggle came acceptance, which we can all learn from.”

Hear hear.

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We are big believers that you should be able to design a life you love and not stick to a linear path, especially when it comes to your career choices. In fact, we'd go as far to say that the concept of retirement in its current form needs to be retired. Yes, that's right, there's no rulebook here!