As Heckerling, Silverstone, Rudd, and company look back, writers are reflecting on the film that helped define an age with its lexicon and fashion. Pop culture journalist Jen Chaney has captured the definitive oral history of the movie, and the title "As If: The Oral History of Clueless ..."
The movie was definitely of the zeitgeist with the way it captured a teen culture's shift away from grunge and set a tone in fashion. Vanity Fair's Julie Miller recently took a look at how director Amy Heckerling and costume designer Mona May created the iconic styles that defined the film and influenced teens for years to come.
Heckerling and May visited Los Angeles schools in the mid-1990s to get a sense of what high-school students were actually wearing—flannel and loose-fitting jeans, none of which fit Heckerling’s ideal aesthetic. “It was just dreadful,” May said of grunge fashion. “The plaid shirts and baggy pants, and girls looked so masculine. There was really none of the girliness.” Knowing that Clueless’s central shopaholic would not be caught dead in flannel, Heckerling and May took wardrobe liberties, creating whimsical costumes that were both smart, feminine, and flattering. “I wanted that feel of a fantasy that you would like to live in,” Heckerling explained. Since there was no Internet or Net-a-Porter, May reasoned that Cher and Dionne would look to runway styles to inform their closets, especially since they had the money to fly overseas to European fashion shows. In addition to drawing on designer wear, the two also incorporated their own style preferences into Cher’s and Dionne’s costumes.
Additionally, it's worth noting, as Grantland's Molly Lambert has, how the landscape of LA is perfectly captured by the film.
Clueless is still a perfect movie, and it’s disheartening that in the 20 years since it came out, Hollywood has gotten no more progressive when it comes to female auteurs. Its ’90s progressive optimism is even more admirable now. Clueless is the rare comedy that really cares, not only for its characters but also its audience. It never condescends to anyone. It’s kind-hearted, with an acid bite. And it makes some bold, Californian claims true to its Jane Austen origins: that vanity and kindness are not incompatible. That just because a girl is really, really pretty and privileged doesn’t mean she is automatically a bad person or your enemy. That beauty is only skin-deep until you make over your soul. That stories about girls and women are not stupid and unimportant, but vital — and the more specific, the better. And that Los Angeles is not by its nature a superficial or stupid place, that it has its own sort of emotional intelligence that has to be understood on its own terms. One of those major terms is its geography, and Clueless is a sprawling portrait of L.A.’s unique beauty.