3. Clueless (1995)

Clueless became an instant style phenomenon with its vibrant, playful approach to 1990s fashion. The film’s iconic plaid skirts, knee-high socks, and matching sets—worn by Alicia Silverstone’s Cher Horowitz—sparked mainstream trends and redefined teen fashion. Serving as a “style bible” for a generation, Clueless continues to inspire designers and fashion enthusiasts alike. Its wardrobe, curated by costume designer Mona May, set the tone for preppy chic and bold accessorizing. According to Elle, the film’s influence is still seen on runways and in street style today.