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The ’90s were Cindy Crawford’s golden years. It was a period when she, along with Christy Turlington, Linda Evangelista, Naomi Campbell and Claudia Schiffer, dominated magazine covers and editorials, signaling the start of the supermodel era. “It was almost like we were a new boy band – we were all different, but we looked good together,” Crawford previously shared.
During these busy years, she forged her own style path, wearing easy denim and leather jackets off-duty, and head-turning dresses on the red carpet. From the siren-red Old Hollywood dress she wore to a Revlon event in 1990, to the iconic harnessed Versace look she wore to a party in 1992, Vogue revisits some of her greatest style hits from the decade.
1992
Modelling that iconic harnessed Versace look.

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1990
Evoking Old Hollywood in a red halter neck and diamonds.

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1997
At the MTV VMAs in a strapless snakeskin dress and a choker.

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1991
Cindy’s off-duty uniform.

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1997
Posing in a lace gown at the Fire & Ice Ball in Los Angeles.

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1996
Sporting a ’90s party top at a movie premiere.

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1995
Bringing knee-highs to the red carpet.

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1990
Another day, another leather jacket for Cindy.

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1991
Showing the back detail of her gown at an event.

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1991
Attending an afterparty in an embellished dress.

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1992
Wearing a Corset and Boret at Emmys.

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1998
Attending a Playboy party in New York wearing a form-fitting red dress.

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1993
Arriving at the MTV VMAs in a beaded slip.

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1996
Arriving at the Blockbuster Entertainment Awards in a silky dress.

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1998
In a printed dress and strappy heels at the premiere of Out of Sight.

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1997
The epitome of ’90s style in a chainmail top.

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1990
Wearing one of her trusty leather jackets.

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1999
Sporting a metallic slip at the annual St Judes Gala in Beverly Hills.

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1992

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1992
In an LBD and feather-trim gloves at Vogue’s 100th anniversary celebration.

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1995
Commanding attention in a bright dress.

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1995
Matching the red carpet in a silky gown.

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1996
Wearing biker leather at a book signing.

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