WATCH: Cindy Crawford's 60 Seconds of Style
Linda Evangelista, 23: THEN
LINDA EVANGELISTA, 52: NOW
Evangelista has worked more or less steadily for the last twenty years. Recent gigs include ad campaigns for Prada, Talbots, and John Galliano.
Cindy Crawford, 26: THEN
The all-American Crawford appeared on hundreds of magazine covers. She also pitched Pepsi (right), hosted the MTV series House of Style, and married the movie star Richard Gere. (They divorced four years later.)
CINDY CRAWFORD, 51: NOW
Re-married in 1998 to businessman Rande Gerber, Crawford has launched several successful businesses of her own, including an eponymous Home Collection and a line of anti-aging skincare products called Meaningful Beauty.
Elle Macpherson, 24: THEN
A leggy blonde Australian known within the industry as "The Body," Macpherson appeared on the cover of the Sports Illustrated Swimsuit Issue a record five times. She also kept a foot in the high-fashion world, walking runways for designers like Azzedine Alaïa and John Galliano.
ELLE MACPHERSON, 53: NOW
The model-turned-entrepreneur's signature lingerie line, Macpherson Intimates, is a best-selling success, stocked at Bloomingdale's, Saks Fifth Avenue, and Neiman Marcus. She's also launched a skincare collection, called (of course) "The Body," and was the host of NBC's Fashion Star. She made a triumphant return to the runway, closing Louis Vuitton's buzzed-about Fall 2010 show. In 2014, Macpherson co-founded WelleCo, the company behind organic wellness supplements such as The Super Elixir ($59; net-a-porter.com).
Helena Christensen, 23: THEN
HELENA CHRISTENSEN, 48: NOW
Christensen co-founded Nylon magazine and acted as creative director, co-owned a New York city boutique, and is now primarily associated with her work as a photographer.
Christy Turlington, 20: THEN
CHRISTY TURLINGTON, 48: NOW
The yoga devotee has launched two active-wear brands, Nuala and Mahnuala, and is a partner in the all-natural ayurvedic skincare line, Sundari. Turlington—who's married to the actor/director Ed Burns—released a documentary, No Woman No Cry, about at-risk pregnant women around the world, visited Capitol Hill to advocate for the Global MOMS act, and co-starred with models Karen Elson and Natalia Vodianova in Louis Vuitton's Fall 2010 ad campaign.
Stephanie Seymour, 22: THEN
Seymour, a face of Almay, Christian Dior, Valentino, and L'Oreal, was one of the first models to sign with the then-fledgling lingerie brand Victoria's Secret; a stormy, multi-year relationship with Guns N' Roses singer Axl Rose further raised her profile. (She appeared in the music videos for "Don't Cry," and "November Rain.")
STEPHANIE SEYMOUR, 48: NOW
She's dabbled in acting, appearing in the 2000 film Pollock and on an episode of Law & Order: Criminal Intent. Seymour has also worked as a contributing fashion editor at Interview and continued to model, most recently for Ferragamo, Hermes, and Valentino.
Naomi Campbell, 23: THEN
Discovered at 15 while window-shopping in London's Covent Garden, Campbell quickly went from being an in-demand catwalk star to posing for numerous magazine covers, many of which had never before featured a black model. She represented Nars, Ralph Lauren, and Prada, appeared in music videos for Madonna, George Michael, and Michael Jackson, and dated Mike Tyson, Robert DeNiro, and Eric Clapton.
NAOMI CAMPBELL, 47: NOW
Although plagued by personal scandals, Campbell is still a fashion-world star. In 2010 Dolce & Gabbana celebrated the 25th anniversary of her career with a party and limited-edition T-shirt; proceeds benefited her charity, Fashion for Relief, which also held a fashion show to benefit Haiti earlier that year. Campbell has recently dabbled in acting, guest starring on Fox’s Empire and American Horror Story: Hotel.
Claudia Schiffer, 19: THEN
CLAUDIA SCHIFFER, 46: NOW
The German-born model is now married to director Matthew Vaughn (Kick-Ass) and has three children. She's a paparazzi favorite, thanks to her chic-mom style and continues to pose part-time for brands like Chanel, Ferragamo, Alberta Ferretti (she acted as the face of their signature fragrance) and Yves St. Laurent.
