Cindy Crawford Then
In the ‘90s, Cindy Crawford was a household name. Her modeling career started in the ‘80s and in the next decade, she appeared constantly on runways, red carpets, and magazine covers. Her most memorable looks were a red Versace gown at the 1991 Oscars (on the arm of then-husband Richard Gere) and those jean shorts in her unforgettable 1992 Pepsi commercial, which aired during the Super Bowl.