Cindy Crawford & Kaia Gerber
In the 1980s and 1990s, no fashion magazine could be considered complete without featuring Cindy Crawford on its cover. She was the most iconic American supermodel, gracing countless magazine covers. Italian fashion designer Roberto Cavalli crafted this printed dress specifically for Cindy.
Cindy first wore it to the 2003 Condé Nast Traveler Readers' Choice Awards in New York City and continued to wear it on various occasions. A decade later, Cindy's then-13-year-old daughter, Kaia Gerber, donned the same dress for a backyard photoshoot.
