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.

adrienne vittadini resort 1986 1987 fashion show
WWD - Getty Images

April 1987

For Ralph Lauren, the supermodel sported a belted chunky sweater, an above-the-knee length skirt, and driving gloves.

ralph lauren fall 1987 ready to wear fashion show and backstage
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November 1987

That same year, she donned an eye-catching graphic sweater for the Perry Ellis runway show.

perry ellis spring 1988 ready to wear fashion show
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April 1988

Next up, she attended the Hooray for Hollywood AIDS Benefit dressed in a semi-sheer chiffon top and sequined skirt.

hooray for hollywood aids benefit april 5, 1988
Ron Galella - Getty Images

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.

thierry mugler runway ready to wear fallwinter 1990 1991
Victor Virgile - Getty Images

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.

second annual revlon's unforgettable women contest winner annoucement
Ron Galella, Ltd. - Getty Images

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.

press conference cindy crawford announces her association with jh collectibles to launch a sportswear line
Ron Galella, Ltd. - Getty Images

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.

fifth annual california industry friends of aids project los angeles apla fashion show and dinner to honor gianni versace
Ron Galella, Ltd. - Getty Images

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.

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Ron Galella - Getty Images

September 1991

All eyes were on Crawford at the 1991 MTV Video Music Awards when she showed up in a sequined, sleeveless black dress.

eighth annual mtv video music awards arrivals
Ron Galella, Ltd. - Getty Images

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.

cindy crawford at fashion show
Vittoriano Rastelli - Getty Images

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.

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Images Press - Getty Images

April 1992

Crawford attended Vogue magazine’s 100th anniversary celebration in a chic Herve Leger bandage dress, feathered gloves, and black pumps.

vogue magazine's 100th anniversary celebration
Ron Galella, Ltd. - Getty Images

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.

44th annual emmy awards
Ron Galella, Ltd. - Getty Images

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.

ninth annual mtv video music awards arrivals
Ron Galella, Ltd. - Getty Images

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.

10th annual mtv video music awards
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September 1994

She donned a gold gown and a voluminous hairstyle at the 1994 MTV Video Music Awards.

11th annual mtv video music awards press room
Ron Galella, Ltd. - Getty Images

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.

cindy crawford attends 5th annual fire and ice ball
Vinnie Zuffante - Getty Images

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.

1995 mtv movie awards
Jeff Kravitz - Getty Images

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.

chanel paris fashion week womenswear spring summer 1996
Stephane Cardinale - Corbis - Getty Images

November 1997

Crawford dazzled in a fitted gold gown and matching oversized shawl while walking down the Todd Oldham runway in 1997.

todd oldham new york
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March 1999

The model wore a show-stopping faded zebra print dress while at a charity event in 1999.

19th annual st jude children's hospital benefit gala
Ron Galella, Ltd. - Getty Images

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.

cindy crawford
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May 2009

Crawford pulled out all the stops for the 2009 Met Gala in a turquoise gown featuring a high side slit.

the model as muse embodying fashion costume institute gala arrivals
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March 2012

She chose a slightly cropped gray blazer, white top, black pants, and boots to attend a John Varvatos benefit in 2012.

2012 john varvatos stuart house benefit
WWD - Getty Images

December 2015

Crawford keeps things easy when she's off the clock in a leather jacket, faded denim jeans, and pointed black boots.

celebrity sightings in los angeles december 11, 2015
GVK/Bauer-Griffin - Getty Images

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.

manus x machina fashion in an age of technology costume institute gala arrivals
Daniele Venturelli - Getty Images

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.

heavenly bodies fashion the catholic imagination costume institute gala
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October 2019

Crawford went with a classic gray-blue two-piece outfit while out and about in the Big Apple.

celebrity sightings in new york city october 10, 2019
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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.

6th annual instyle awards arrivals
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February 2022

For Off-White's Paris Fashion Week show, fans caught her in a tiered tulle skirt, cropped blazer, and a graphic tee.

off white runway paris fashion week womenswear fw 2022 2023
Taylor Hill - Getty Images

May 2023

Recently, Crawford was snapped in a sweet white lace dress while at a charity event in Los Angeles.

the 6th annual best buddies' celebration of mothers
Stefanie Keenan - Getty Images

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