Cindy Crawford may be one of the original “supermodels” of the ‘90s, but her all-American looks, signature beauty mark and business smarts have helped her to transcend the fashion world and become a household name. From the moment Crawford moved to New York City in 1986, the Illinois native was an immediate success. Within months, she landed her first American Vogue cover and racked up credits that included working with fashion photographer greats such as Richard Avedon and Patrick Demarchelier, and walking the runway for the likes of Calvin Klein and Ralph Lauren.
But that was just the beginning. The ‘90s were perhaps the most impactful decade of Crawford’s career, starting with a British Vogue cover (alongside fellow supers Naomi Campbell, Linda Evangelista, Tatjana Patitz and Christy Turlington), which led to a starring turn in George Michael’s “Freedom! ‘90” music video and a now-iconic walk down the Versace runway. With that newfound recognition came opportunities outside of the modeling world, including the launch of at-home workout videos, a hosting gig for MTV’s House of Style and a major Pepsi commercial. Of course, that meant more style moments from Crawford, who was partial to high-waisted jeans and leather jackets or oversized blazers thrown over miniskirts on her more casual days. On the red carpet, the model always made a lasting impression, whether she opted for a floor-length gown with strategic cut-outs or a fitted minidress (often in red, and almost always Versace).
Though Crawford announced her retirement from full-time modeling in 2000 (and again in 2016), it hasn’t entirely stuck. The supermodel has since returned to the runway and starred in fashion campaigns for special occasions, and Crawford is frequently spotted in the front row or on the red carpet, cheering on her daughter, Kaia Gerber, as she pursues a modeling career of her own.
Ahead, you’ll find a mix of Crawford’s greatest fashion moments on and off the runway—from the infamous Versace dress that changed the red carpet forever to her current street style outfits that recall her timeless model-off-duty looks.
1988, Calvin Klein Runway
One of Crawford’s earliest runway shows was with Calvin Klein, where she wore several designs, including this strapless column gown. Nearly 30 years later, Crawford’s daughter Kaia Gerber made her runway debut on the Calvin Klein catwalk during the brand’s fall 2018 collection show at New York Fashion Week.
1990, Thierry Mugler Runway
Crawford may not have done as many runways as her peers, but she still appeared in shows for some of the most influential designers around the globe. This look from Thierry Mugler’s fall 1990 collection at Paris Fashion Week featured plenty of sparkling embroidery throughout the fitted jacket, paired with fishnets and a massive embellished choker for a truly memorable moment.
1990, Revlon Event
Red would become a go-to color for Crawford on the red carpet, and this mini halter dress, which she wore to attend a Revlon event, remains one of her best. Crawford, who became the face of Revlon in 1989 (and worked with the brand until 2000), gave the dress an Old Hollywood twist with a classic red lip and manicure, as well as oversized diamond jewelry.
1991, California Industry Friends Of AIDS Project
For a benefit event honoring Gianni Versace, Crawford chose a high-neck, satin dress (presumably Versace) that looked simple enough from the front. But the classic black gown had a colorful twist at the back, with criss-crossing pieces of fabric in neon colors. A thigh-high slit made for another bold element, and Crawford chose a statement cuff bracelet and shoulder-grazing earrings to complete the look.
1991, In Los Angeles
Before the days of street style looks curated by a team of stylists, off-duty photos were a more authentic glimpse into celebrities’ personal style. This model-off-duty moment from Crawford may not have been professionally styled, but it’s still a timeless look, composed of high-waisted Levi’s 501 jeans, a black turtleneck and a black leather Azzedine Alaïa jacket.
1991, Versace Runway
Crawford has called this Versace show her “favorite fashion moment,” one that saw her joined by fellow supermodels Naomi Campbell, Linda Evangelista and Christy Turlington for the finale. The models (plus Tatjana Patitz) had recently appeared in George Michael’s “Freedom” music video, and Gianni Versace ended his fall 1991 collection with the hit song. “Gianni had the song playing, and the four of us come out together,” Crawford recalled in a video with Vogue. “It was one of those moments where music, and pop culture, and fashion all came together in a super magical way.”
1991, Academy Awards
Crawford’s red Versace dress at the 1991 Oscars is one of the award show’s most iconic fashion moments, as it marked the first time that a Versace gown had ever graced the red carpet. The column dress was custom-made for the model by Gianni Versace, and featured a plunging neckline, open back and ultra-high slit, which Crawford paired with her signature beauty look: volumized waves and barely-there makeup in soft brown shades.
1992, MTV Video Music Awards
As the host of MTV’s House of Style series, Crawford was on hand at the 1992 VMAs to get all of the fashion details from the guests. Of course, Crawford’s own Versace gown, which first made its way down the runway as part of the fashion house’s fall 1992 Miss S&M collection, stole the show. The harness-bodice may have caused a bit of a stir at the time, but it’s a look that would be recreated on more than one occasion in the future: by Crawford’s own daughter, who wore a new, custom take for her 18th birthday in 2019, and nearly identically styled by singer Dua Lipa at the 2022 Grammy Awards.
1993, Chanel Runway
The one-shoulder gown that Crawford wore as part of the Chanel spring 1993 couture show was such a standout look that actress Margot Robbie eventually had the dress remade for the 2023 Met Gala. Crawford’s original design by then-creative director Karl Lagerfeld included a twisted sweetheart neckline with layers of draped fabric and a corseted midsection of PVC material with black and gold boning.
1994, Fire & Ice Ball Benefit
For the 1994 Fire & Ice Ball benefiting Revlon’s cancer research program at UCLA, Crawford chose a black column gown that featured a sweetheart neckline and satin stripes. The model completed the look with minimal jewelry and matching black sandals, a handbag and fur stole.
1995, ‘Batman Forever’ Premiere
Nearly 20 years before her husband Rande Gerber teamed up with George Clooney for their Casamigos tequila, Crawford posed on the red carpet with the actor at the Batman Forever premiere (Clooney would later go on to play Batman just a few years later). Crawford’s oversized black suit was a staple look for her at the time—both on and off the runway—and for the film’s premiere, she kept the whole thing more casual with a white tank top underneath.
1995, MTV Video Music Awards
Crawford skipped the floor-length gowns at the 1995 MTV VMAs in favor of a fitted red bandage dress, which she paired with matching strappy sandals, a chic scarf and a tiny pouch bag.
1997, Valentino Runway
Model makeovers on the runway are pretty commonplace now, but Crawford’s blonde look at the 1997 Valentino couture show was a major transformation. The model showed off her temporary blonde updo in several designs during the show, but when paired with this shimmering silver and blue one-shoulder dress, Crawford sported the ultimate icy look.
2000, Macy’s Benefit Event
Roberto Cavalli is another red carpet favorite of Crawford’s, and in 2000, she wore this leopard-print design to a benefit fashion show in Santa Monica. The floor-length slip dress was part of the fashion house’s fall 2000 collection, and it featured darker sections that perfectly matched Crawford’s darker hair color.
2003, Dream Halloween Fundraising Event
By the early 2000s, red carpet events became a family affair for Crawford, who had since married Rande Gerber and given birth to two children, Presley and Kaia. In 2003, Crawford was joined by the whole family for an event benefiting the Children Affected By AIDS Foundation, where she posed alongside a one-of-a-kind Barbie doll. Matching the model right down to her beauty mark, the Barbie wore a feathery pink gown just like Crawford’s strapless Roberto Cavalli number.
2007, Versace Event
In 2007, Crawford reunited with model Naomi Campbell for the Rodeo Drive Walk of Style Awards, which honored Versace that year. For the occasion, Crawford chose a metallic purple gown from the Italian fashion house, and she switched up her hair for a longer, sleeker style.
2009, Met Gala
Crawford attended her first Met Gala in 2009 for the museum’s The Model As Muse: Embodying Fashion exhibit, which she also happened to be featured in. For fashion’s biggest event of the year, Crawford turned to Versace for a satin blue gown that she paired with matching platform sandals and a clutch.
2013, Cannes Film Festival
The Cannes Film Festival calls for an all-out glamorous moment, and Crawford delivered at The Great Gatsby premiere with a white Roberto Cavalli gown that featured an embellished gold neckline. Crawford added strappy gold heels and yellow diamond drop earrings, as well as a volumized blowout and a shimmering brown smokey eye to complete the look.
2015, In London
In 2015, Crawford celebrated the launch of her book, Becoming, with signings in major cities all over the world. In London, she hosted a party alongside Casamigos, wearing a Victoria Beckham midi dress that featured a one-shoulder silhouette and white paneling along the skirt.
2015, Balmain x H&M Event
Before officially joining the modeling world, Kaia Gerber attended plenty of red carpets and runway shows with Crawford. For the Los Angeles event celebrating Balmain’s collaboration with H&M, the mother-daughter duo arrived in coordinating ensembles. While Gerber went with a long-sleeved minidress, Crawford stuck with some of her styling staples in a black blazer and leather pants. The following year, Crawford would star in a campaign for the French fashion house (along with Naomi Campbell and Claudia Schiffer), and she would even attend the Met Gala with the brand’s creative director, Olivier Rousteing.
2017, Versace Runway
Crawford has referred to Gianni and Donatella Versace as family, so it’s no surprise that she returned to the runway for Versace’s spring 2018 collection. Marking 20 years since Gianni’s death, the collection served as a tribute to the fashion house’s founder, with Crawford walking hand-in-hand with models Carla Bruni, Claudia Schiffer, Naomi Campbell and Helena Christensen—all in gold mesh gowns.
2017, In Paris
Crawford’s model-off-duty looks of the ‘90s were so timeless that more than 20 years later, she’s still rocking a similar look. While in Paris, the model paired light wash, straight-leg jeans with a white t-shirt, black leather jacket and open-toe heeled boots.
2017, Chanel Show
While cheering on her daughter, who walked in Chanel’s spring 2018 collection, Crawford showed that she’s still a fan of a tailored look (and a bombshell blowout) in a head-to-toe Chanel ensemble that included black trousers, a cream blouse and a matching cream jacket.
2018, Met Gala
Crawford returned to her red carpet roots at the 2018 Met Gala, wearing a red Versace gown with a plunging neckline and curve-accentuating silhouette that appeared to reference the model’s 1991 Oscars dress.
2018, In New York City
While in New York for fashion week, Crawford showed off another flawless street style look, pairing straight-leg jeans, a white t-shirt and a statement coat with snakeskin mules, a white clutch and sunglasses.
2018, British Fashion Awards
The whole Crawford-Gerber family was on hand at the 2018 British Fashion Awards, where Kaia took home the Model of the Year award. While Kaia was dressed in a cut-out metallic Alexander McQueen number, Crawford went for a more understated look in a velvet, off-the-shoulder column gown by Marchesa.
2021, InStyle Awards
Crawford made a splash at the 2021 InStyle Awards in a shimmering gown from Missoni’s spring 2022 collection, with zig-zags of colorful paillettes.
2022, Off-White Runway
Following the passing of Off-White founder Virgil Abloh, Crawford made another runway appearance with a crew of famous models past and present, including Naomi Campbell and her daughter Kaia. For her runway return, Crawford wore a tiered tulle skirt and a cropped blazer from the designer’s last collection.
2022, The Albie Awards
At the end of 2022, Crawford and her husband headed to New York City to celebrate the inaugural Albie Awards, hosted by George and Amal Clooney’s human rights organization, the Clooney Foundation For Justice. For the occasion, Crawford wore a black column gown by Jason Wu, which featured an asymmetric neckline and was styled with Aquazzura sandals, a Carolina Herrera clutch, and Lorraine Schwartz diamonds.
2023, ‘The Super Models’ Screening
As the subjects of the Apple TV+ documentary The Super Models, Crawford, Campbell, Evangelista and Turlington debuted a new Vogue cover over 30 years after their first cover together (model Tatjana Patitz, who was also part of the original shoot, passed away in early 2023). Landing the September cover for American and British Vogue was just part of the models’ celebration, which also included a screening of the documentary in London, where Crawford wore this Versace cut-out dress.
2023, Clooney Foundation For Justice’s The Albies
In a purple Versace dress featuring safety pin details, from the brand’s latest Milan runway show.