Original 90s Supermodel Cindy Crawford’s Hollywood Romances Revealed

She’s a big fan of a low-key wedding.

Cindy Crawford is known for being a supermodel that defined a new era of fashion, the rollicking 90s fashion scene, which we are sure to relive again as we watch Apple TV’s upcoming The Super Models documentary.

The series will cover the style icon’s rise to fame, alongside other names dominating the modelling world at the time, including Linda Evangelista, Christy Turlington and Naomi Campbell.

There’s a lot to be said of Crawford, who entered the zeitgeist at a time where fashion was saturated with blue-eyed blondes. As a brunette with a straight A-average, she paved a new niche, one that her own daughter Kaia Gerber continues to this day.

Cindy Crawford is due to star in new series ‘The Super Models’. (Credit: Image: Getty)

Crawford’s career skyrocketed, and she still puts this down to one integral moment: the 1991 Fall Versace show, where Naomi Campbell, Christy Turlington, Linda Evangelista and Cindy Crawford walked the runway to George Michael’s ‘Freedom! ‘90’.

“The highlight of my career was, I think, that supermodel moment when Linda, Christy, Naomi and I came out for a Versace show to a George Michael song which we had just done the video for,” she told The Daily Record. “It was like a frozen moment in time – that moment defined supermodel.”

However, every rising star faces equal interest in their personal life as their professional, and Crawford’s romantic, and now family life, is as Hollywood as it gets. Here, we take a look back at her romantic history.

1991 – 1995: Richard Gere

The couple were together for several years. (Credit: Image: Getty)

A young Cindy met Richard Gere back in 1988, at a barbecue hosted by a photographer she knew. Crawford was only 21, and Gere 38, but they fell for one another despite the 17-year age gap.

It appeared from the outside an uncomplicated romance, two beautiful people who had become a power couple. They appeared at the 1991 Academy Awards together and in December of that year, they eloped.

This was at the height of her fame (and that iconic Versace show), but Crawford went down the aisle to marry Hollywood heart-throb Richard Gere with aluminum foil rings.  

Of course, Gere had become a household name with the likes of An Officer And A Gentleman (1982), Breathless (1983) and of course, Pretty Woman (1990).

“Richard [Gere] and I had been dating for several years, and at one point, I was like, ‘Are we doing this or what?’ And he said, ‘Let’s go to Vegas tonight,'” Crawford told Yahoo Entertainment. “It wasn’t the wedding I dreamed of. It was so last minute I wore this Armani suit. It was a nice Armani suit, but I didn’t dream of getting married in a navy blue suit. And the ring was made out of tinfoil because it was so last minute. But I did have Herb Ritts as my bridesmaid — and taking the pictures!”

Despite their time together, the couple eventually divorced in 1995. There were a lot of factors at play, but Crawford told People it was in part the little time they got to spend together in their busy schedules, but also the age gap.

Crawford told Oprah’s Master Class, “I just think your 20s for women is such a time when you’re starting to come into your own and feel your own power and connect to your inner strength, and it’s hard to do that — it’s hard to change — in a relationship, because what one person might have signed up for, all of a sudden, you’re not that anymore.”

1998 – Present: Rande Gerber

Crawford with her husband Rande Gerber. (Credit: Image: Getty)

It turns out that Crawford met her future, long-term husband Rande Gerber when she was still with Gere. She told Harper’s Bazaar that she had attended her agent’s wedding (which Gere didn’t want to attend) and met Gerber who also had a girlfriend at the time.

“That’s the best time to meet someone because that’s when you’re truly yourselves. We became friends and after Richard and I broke up then we started dating,” she said.

She believes it was the bonds of their early friendship that remains key to their enduring love and affection for one another.

In Oprah’s Master Class she explained, “We really listen to each other. I would want that friendship in my life no matter what.”

Gerber is an American businessman and former model, who grew up in New York. He runs the Gerber Group, which opened its first venue in 1991. He went on to partner with George Clooney to launch Casamigos Tequila, later selling the brand for millions.

After dating in the mid-90s, Crawford walked down the aisle again, this time in a secret Bahamian wedding in May 1998.

The pair wasted no time having children, welcoming their first child, a son, Presley Walker Gerber in July 1999. Naturally, Presley is now a model with IMG Models. Then, a second child, a daughter, was born, named Kaia Jordan Gerber. She has since become a verified ‘it-girl’ and well-known model herself. Kaia is currently dating Elvis actor, Austin Butler.

Cindy and Rande with their daughter Kaia. (Credit: Image: Getty)

While Cindy, already familiar with the pitfalls of modelling, may have wanted her children to do something else, she has been nothing but supportive of her children’s dreams.

“I have no concerns with Kaia wanting to do [modelling] and she respects me because I’ve been there and I feel like I’ve been a great mentor,” she told Vogue.

It appears that despite the enduring years, Crawford and Rande Gerber’s relationship (and dedication to their family) remains strong.

She told Redbook in 2011 that the secret to their long-standing romance is ‘date nights’.

“It sounds a little cheesy, but that’s what it is – time for the two of us,” she said, adding that she enforced a strict ‘bedtime’ rule with her children so that she could have some time alone with her husband.

In 2022, her husband Rande Gerber gushed about the love of his life.

There are so many things I love about her,” he told Haute Living. “She’s still a small-town girl at heart. The most important thing to Cindy is her family and making sure that we’re all happy. She’s so low-key despite her high-profile position. She’s someone who constantly gives back, who does so many things for so many people without asking for anything in return. She means the world to me.”

The pair have gone from strength to strength with their 25-year marriage, and it appears it’s only further up from here.  

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