Celebrities

The most iconic photos of Cindy Crawford through the years

Happy birthday, Cindy Crawford! The beauty turns 55 on Feb. 20, 2021, and in honor of her big day, Wonderwall.com is rounding up some of the most iconic photos of the supermodel over the years. Keep reading to take a look back, from iconic snaps in Vogue to sweet family moments… Let’s start with this gorgeous lady in red! Cindy attended the Second Annual Revlon Unforgettable Women Contest in 1990 rocking a vibrant red dress and red lip. 

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This 1988 photo comes right from the pages of Vogue! Cindy Crawford posed for the revered fashion magazine that year — Arthur Elgort was the photographer — in a silk Versace slip dress with a wool coat over top.

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After finding fame as a model, Cindy Crawford started dating actor Richard Gere. The two are seen here in 1991, the same year they married.

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On the catwalk! Cindy Crawford strutted her stuff at the Dolce&Gabbana show in Milan in the fall of 1991. 

Back in 1991, Cindy Crawford showed off her excellent airport style after touching down at LAX in Los Angeles. She rocked a leather jacket, a black turtleneck and jeans — a classic outfit that would still be in style today. 

In 2017, Cindy Crawford made headlines for her iconic participation in the Versace Ready to Wear Spring/Summer 2018 fashion show in Milan alongside other legendary supermodels Carla Bruni, Claudia Schiffer, Naomi Campbell and Helena Christensen. 

Stunning! Cindy Crawford was on hand as then-beau Richard Gere’s date at the 1984 Academy Awards. 

Cindy Crawford attended the Love Ball in New York City in 1989 rocking black leather and a red lip — her signature during the era.  

In 1997, Cindy Crawford brought then-boyfriend Rande Gerber — a model-turned-restaurateur at the time — to the premiere of “Father’s Day.” The couple married the following year. 

Cindy Crawford reunited with photographer Arthur Elgort (yes, he’s actor Ansel Elgort’s father) for Vogue in 1992. She posed in a Giorgio Armani sequined minidress in a vintage convertible for the iconic pic. 

She’s still got it! Cindy Crawford lit up the Empire State Building in New York City in March 2020 just a few weeks after her 54th birthday.

In 2006, Cindy Crawford brought along daughter Kaia Gerber for the Runway for Life event benefiting St. Jude Children’s Research Hospital in Beverly Hills. 

All grown up! Cindy Crawford brought along daughter Kaia Gerber once more over a decade later… to the 2018 Fashion Awards in London after Kaia had started modeling herself.

Cindy Crawford arrived in style at the Fifth Annual California Industry Friends of AIDS Project Los Angeles Fashion Show and Dinner to Honor Gianni Versace in 1991. 

Cindy Crawford was a vision in electric blue at her very first Met Gala appearance in 2009. That year, the theme was “The Model as Muse: Embodying Fashion.” She attended with Donatella Versace while dressed in a custom gown from the fashion house. 

Cindy Crawford brought along her two kids — son Presley Gerber and daughter Kaia Gerber — to an Alex’s Lemonade Stand event in Hollywood in 2010. Prior to this event, Cindy hadn’t put her kids in the spotlight very often.

In 1993, Cindy Crawford was on hand for the Chanel Haute Couture Spring/Summer show in Paris where she rocked this all-red monochromatic look on the runway. 

When it came time for Cindy Crawford to attend the 2018 Met Gala, she opted for a vibrant red Versace gown, which over the years certainly became her signature color.

A blonde Cindy Crawford? In 1997 the supermodel hit the 1997-1998 Fall/Winter Haute Couture Valentino show in this shocking hair color.

Cindy Crawford got all dolled up for Halloween in 2018 with a themed family costume. The supermodel, hubby Rande Gerber and kids Presley Gerber and Kaia Gerber dressed up as famous rock stars for Rande’s annual Casamigos tequila Halloween party. 

For Paris Fashion Week back in 2018, Cindy Crawford was on hand for the Saint Laurent show. She posed in front of the iconic Eiffel Tower. 

Cindy Crawford was on hand for Versace’s “Rock ‘N Rule” Fashion Show Gala benefiting amfAR in New York City back in 1992. She rocked a strappy black and gold look from the fashion house. 

For the launch of the Cindy Crawford Capsule with Re/Done collection in 2017, Cindy brought along look-alike daughter Kaia Gerber. Both ladies donned denim for the occasion, with Cindy adding a sleek black leather jacket.

For the Fall 1994 Isaac Mizrahi fashion show, Cindy Crawford was on hand in a black coat, tights and pink booties. 

It was a family affair at the Sies Marjan Spring/Summer 2019 show during New York Fashion Week in 2018. Cindy Crawford brought along hubby Rande Gerber and kids Kaia Gerber and Presley Gerber for the event.


























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