‘You Try Driving In Platforms’: How ‘Clueless’ Created The Style That Made It A Pop Culture Icon

Rarely does a year goes by that people don’t celebrate the greatness of Clueless and its impact on pop culture. Twenty years after the film was released, people of all ages still use phrases popularized by the film like “As if!” and “Whatever!” in casual conversation, and we’re willing to bet that there are quite a few people who still reference Monet when it has absolutely nothing to do with art.

But perhaps more than the lines and the actors that delivered them, the clothes featured in Clueless made a lasting impact as well, making it not only a quintessential ‘90s movie, but a timeless cultural juggernaut as well — one that continues to speak to generation after generation. (It probably also doesn’t hurt that the film absolutely nailed the cliques and stereotypes of just about everyone’s high school experience.)

That’s why we wanted to talk to Clueless writer and director Amy Heckerling and costume designer Mona May about the thinking that went in to creating the overall look and feel of the film. We also spoke to actors Wallace Shawn and Justin Walker to learn as much as we could about the styles that were created on a very limited budget for a movie that was almost never made.

You Argued Your Way From A C+ To An A-?

… a lot of the people who liked it liked the world that it was showing and they found that more agreeable than the dog-eat-dog world that Reagan and his followers had represented.

Long before she introduced the world to Cher Horowitz and Dionne Davenport, Amy Heckerling proved that she had a knack for teen stereotypes and comedy when she directed 1982’s “Fast Times at Ridgemont High,” which was written by Cameron Crowe. (She also directed the hilarious and absurdly underrated “Johnny Dangerously,” but that’s another movie for another time.) However, “Clueless” was all Heckerling and like “Fast Times” it was sharp and intelligent, and of course the studios didn’t recognize that at first. Fortunately, Scott Rudin came along and slapped some sense into the film industry. With a small budget and a cast of mostly unknown actors, Heckerling and her friend Mona May set out to create something magical, both in fashion and language, and exceeded everyone’s expectations.

Amy Heckerling, Director: I went to Fox with this pilot I had written, which was just about 20 minutes for a TV show but I liked the character a lot. When my agent at the time, Ken Stovitz, read it he said, “This character should be in a feature,” and he showed it to them. They agreed and I developed it with them, but they had very specific ideas and I wrote a draft and they wanted me to do things to it, and I did and they still didn’t want to make it. Then, when he tried to sell that, because it was in turnaround, nobody wanted it. So, it was very hard. Also, at the time, some youth-oriented movies came out that seemed to be about less intelligent young people and they didn’t do so well, so they figured this movie was just like those so they didn’t want it.

These are movies that I thought were very funny: there was one with Adam Sandler and Steve Buscemi, Airheads. I guess that didn’t perform the way they wanted it even though I thought it was great. And there was also one called PCU, Politically Correct University. It had Jeremy Piven and David Spade and they were great and it was a really cool concept. This movie sounded like those and we’re not making that kind of movie now. Also female, so forget about that. It was in turnaround for a long time till Stovitz got it to Scott Rudin and he liked it. It went from everybody passing on it to a bidding war because people suddenly, what they hate they like. They really stand by it [laughs]. Whatever.

Mona May, Costume Designer: We actually met before Clueless. She was doing a pilot for television about these two young girls living in New York City and I interviewed with her. Right away we hit it off creatively. So, we got to work on this pilot and really fell in love with each other creatively. Just really, really fun. I loved her fashion sense. She’s really well-versed in fashion. And the pilot unfortunately didn’t get picked up but our relationship was formed. She knew I grew up in Europe; I very much have the European aesthetics and more a European sense of fashion. When she did Clueless she called me up and said, “Mona, I really want you to do this movie.” So, that’s how it happened.