Cindy Crawford's Career Evolution: From Fashion Model To Global Powerhouse
At 57, the OG super continues to inspire and shine.
By Shermin Ng - published
In an epic career spanning over three decades, Cindy Crawford has hit countless milestones—from fashion campaigns, music videos and commercials to her own beauty line—and has proven to be an enduring force within the fashion industry and beyond.
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Today, the iconic supermodel, business mogul, wife to restaurateur Rande Gerber and mum to models Presley and Kaia Gerber—as well as four-time cover star of Harper's BAZAAR Singapore—continues to inspire and shine. We take a closer look at the OG super's rise to fame and her major career milestones throughout the years.
1980s: Beginnings of a supermodel
Crawford started her modelling career when she won the Elite Look of the Year award at the age of 17. After earning a scholarship to study chemical engineering at Chicago's Northwestern University—which she attended for one semester—she moved to New York City and signed with Elite New York modeling agency in 1986.
Crawford posed nude for her first Playboy magazine shoot in 1988 (and another in 1998) and was ranked fifth on Playboy's list of the 100 sexiest stars of the 20th century. She went on to become the face of US cosmetics giant Revlon in 1989, her first major contract, for 11 years.
1990s: The ascent
The widespread appeal of Crawford lay in her all-American looks, trademark facial mole, and athletic physique. She was featured together with top models Christy Turlington, Linda Evangelista, Tatjana Patitz, and Naomi Campbell on the cover of the January 1990 edition of British Vogue, and the models appeared in the music video for George Michael's Freedom! '90 later that year.
The nineties saw the supermodel grace hundreds of covers of leading fashion magazines—including Harper's BAZAAR, Cosmopolitan, Allure, and W—and walk the runway for the likes of Chanel, Versace, Dolce&Gabbana, Christian Dior, Calvin Klein and Ralph Lauren.
Crawford was invited to the Oscars for the first time in 1991, and the iconic red number she wore was the first-ever Versace dress worn on the Academy Awards red carpet. The striking piece with a plunging neckline was the subject of many replicas, and is still referred to as one of the best dresses in Oscars history.
From 1989 to 1997, Crawford was a host and executive producer of MTV's House of Style—it arrived at a time of supermodel mania and gave her the opportunity to conduct interviews that connected with a younger audience.
The supermodel took on the at-home fitness market in the '90s and her workout videos—Cindy Crawford: Shape Your Body in 1992 and Cindy Crawford: The Next Challenge in 1993—developed with celebrity trainer Radu Teodorescu, were hugely successful.
In 1992, she starred in her iconic Pepsi Super Bowl ad after signing a multi-million dollar deal with the soda brand. Three years later, she made her film debut in Fair Game alongside William Baldwin. 1995 also marked the year Crawford joined the Omega family; she is the Swiss watch brand's longest-running brand ambassador till date.
In the late 1990s, Crawford made a number of appearances in magician David Copperfield's stage shows, standing in for her fellow supermodel Claudia Schiffer as Copperfield's guest assistant. She took part in a number of different illusions, including being levitated and sawn in half.
Related article: OG Supermodel Cindy Crawford Continues To Ride High At The Top Of Her Game
2000s: Building her brand
After quitting full-time modeling in 2000, Crawford started Meaningful Beauty with cosmetic surgeon Dr. Jean-Louis Sebagh in 2004. She also dabbled in furniture and home design with Cindy Crawford Home and launched a home goods line with JCPenney in late 2009.
In the same year, Crawford was one of many celebrities—including George Clooney, Donald Sutherland, and Lindsay Lohan—to be intimately photographed by English musician, photographer, and film director Deborah Anderson at the Peninsula Hotel for Room 23, a fine art coffee table book.
2010s: An enduring force
In 2011, Crawford starred as John Taylor in Duran Duran's music video for Girl Panic, featuring '90s supermodels as the band members. She was also the Headmistress in Taylor Swift's 2015 Bad Blood music video, which saw cameos from A-listers including Selena Gomez, Jessica Alba, Gigi Hadid, Cara Delevingne and Lily Aldridge.
In 2016, the supermodel brought her role in George Michael's 1990 Freedom music video to real-life on Lip Sync Battle for Zachary Quinto's performance.
Becoming, a book chronicling the supermodel's life and career co-written by Crawford and Katherine O'Leary, was published in September 2015. The following year, Crawford and her daughter Kaia appeared together on the cover of an international fashion title for the first time.
Along with models Claudia Schiffer, Naomi Campbell, Helena Christensen and Carla Bruni, the OG super closed the Versace spring/summer 2018 fashion show, which paid tribute to the late Gianni Versace.
2020s: The legacy continues
Crawford was featured in a four-part Apple TV+ docuseries titled The Super Models, alongside fellow supers Naomi Campbell, Christy Turlington, and Linda Evangelista who revisited her modelling careers. It premiered on September 20, 2023.
Her legacy, of course, also lives on through her daughter Kaia, who is certainly following in her mother's footsteps in the fashion world.