See Photos of Cindy Crawford's 32 Most Iconic Style Moments
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Cindy Crawford is considered one of the greatest supermodels of all time. After winning the Elite Look of the Year Award in the early 1980s, she began working with major fashion houses like Chanel, Thierry Mugler, and Ralph Lauren. Off the runway, she appeared in famous ads (remember her Pepsi commercial?), penned several books, guest starred on television shows, and was briefly married to A-list actor Richard Gere.
Through it all, she's had more memorable style moments than we can count, many of which are still talked about today. Ahead, we rounded up several of our favorites, so scroll through and enjoy.
August 1986
Crawford wore a fun, polka-dotted mini dress with a floppy hat and an oversized beaded necklace for the Adrienne Vittadini show.
April 1987
For Ralph Lauren, the supermodel sported a belted chunky sweater, an above-the-knee length skirt, and driving gloves.
November 1987
That same year, she donned an eye-catching graphic sweater for the Perry Ellis runway show.
April 1988
Next up, she attended the Hooray for Hollywood AIDS Benefit dressed in a semi-sheer chiffon top and sequined skirt.
March 1990
In 1990, Crawford strutted down the Thierry Mugler runway in a sparkly one-piece outfit with fishnet tights and a bedazzled choker. It was a standout ensemble in every way.
August 1990
Later that year, the star turned heads at a Revlon event when she showed up in a deep red halter-neck dress matched with diamond jewelry. The event that night was held in New York City at the Metropolitan Museum of Art.
August 1990
Later that month, she leveled up a casual graphic tee, varsity jacket, and a belted mini skirt with tights and a pair of black pumps for a press conference.
February 1991
The California Industry Friends of AIDS Project Los Angeles event was thrown in honor of Gianni Versace, and to celebrate, Crawford went all out in a satin dress featuring a lime green and orange back.
March 1991
The star attended the 1991 Academy Awards with actor Richard Gere in a timeless red dress with a plunging neckline. The model and actor had a six-year-long relationship.
September 1991
All eyes were on Crawford at the 1991 MTV Video Music Awards when she showed up in a sequined, sleeveless black dress.
October 1991
For a 1991 Dolce and Gabbana show, she floated down the runway in a graphic mini dress, black elbow-length gloves, and over-the-knee tights.
January 1992
She also walked the Ralph Lauren runway during New York Fashion Week in a bright white halter-neck dress with a flared skirt.
April 1992
Crawford attended Vogue magazine’s 100th anniversary celebration in a chic Herve Leger bandage dress, feathered gloves, and black pumps.
August 1992
Crawford looked sleeker than ever at the 1992 Emmy Awards in a tuxedo-inspired ensemble with strappy black heels and a matching beret.
September 1992
The 1992 MTV Video Music Awards welcomed Crawford in a distinct buckled and bedazzled Versace number that Dua Lipa wore two decades later for the 2022 Grammys. Proof that the supermodel’s style is indeed timeless.
September 1993
A year later, she decided to go with a spaghetti-strapped black dress, pointed-toe heels, and statement necklaces for MTV’s annual awards ceremony.
September 1994
She donned a gold gown and a voluminous hairstyle at the 1994 MTV Video Music Awards.
December 1994
That same year, Crawford attended the Fire and Ice Ball dressed in a navy-black gown with ribbon detailing and a small stole.
June 1995
Crawford loves a red look. Here, she’s seen arriving at the 1995 MTV Movie Awards sporting a red fitted mini dress with a red scarf and sandals.
October 1995
During Paris Fashion Week in 1995, Crawford was captured backstage with fellow supermodel Claudia Schiffer during the Chanel ready-to-wear spring/summer 1996 show. The two wore pastel looks with khaki pants, leather belts, and cropped white sweater tops.
November 1997
Crawford dazzled in a fitted gold gown and matching oversized shawl while walking down the Todd Oldham runway in 1997.
March 1999
The model wore a show-stopping faded zebra print dress while at a charity event in 1999.
September 2002
Crawford looked like a dream in green when she was captured on camera in 2002 wearing a chartreuse button-down top with sleek black sunglasses.
May 2009
Crawford pulled out all the stops for the 2009 Met Gala in a turquoise gown featuring a high side slit.
March 2012
She chose a slightly cropped gray blazer, white top, black pants, and boots to attend a John Varvatos benefit in 2012.
December 2015
Crawford keeps things easy when she's off the clock in a leather jacket, faded denim jeans, and pointed black boots.
May 2016
Balmain designed her dress for the 2016 Met Gala. It was a striking silver gown that certainly stood out on the red carpet.
May 2018
She attended the Met Gala again in 2018, and this time, she wore her favorite color red, courtesy of Versace. The camera couldn’t get enough of her that night.
October 2019
Crawford went with a classic gray-blue two-piece outfit while out and about in the Big Apple.
November 2021
Crawford posed with her daughter Kaia Gerber while walking an awards red carpet in 2021. The mother-daughter duo wore sleeveless sequined dresses that evening.
February 2022
For Off-White's Paris Fashion Week show, fans caught her in a tiered tulle skirt, cropped blazer, and a graphic tee.
May 2023
Recently, Crawford was snapped in a sweet white lace dress while at a charity event in Los Angeles.
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