Clueless (1995) is director Amy Heckerling’s sharp, stylish update of Jane Austen’s classic novel Emma. The film follows the wealthy and popular Beverly Hills teenager Cher Horowitz (Alicia Silverstone) as she navigates high school, charting her evolution from well-intentioned but shallow matchmaker to someone capable of empathy and genuinely improving the lives of those around her. Both a satire and celebration of 1990s youth culture, the film captures the dynamics of teenage friendship, social hierarchies, and the decade’s ever-evolving fashion. Using bold plaid prints and coordinated sets, costume designer Mona May made wardrobe choices that became instant cultural touchstones. The film’s fashion shaped real-world trends, influenced designers for decades to come, and spoke to the film’s preoccupa...