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Read This: An oral history of the over-the-top fashion of Clueless


This being the year of Clueless’ 20th Anniversary, tons of retrospectives are popping up across the internet. One that’s well worth a read is an oral history assembled by Uproxx that explores the film’s unique sense of style. Writer-director Amy Heckerling and costume designer Mona May provide the bulk of the interview with actors Wallace Shawn (a.k.a. Mr. Hall) and Justin Walker (a.k.a. Christian Stovitz) on hand to give their perspectives as well.

It turns out Heckerling and May were friends before the project and grew even closer as they tried to costume an entire school full of fashion-forward students—including 60 costume changes for the lead girls—all on a relatively small budget. May explains:

So much of creating films, directors can be male… not understanding fashion and maybe even afraid of it. And [Heckerling] was completely full on and understood how important fashion is in the film. She has amazing sense of fashion and that is incredibly helpful to a designer on a movie. The collaboration is so much more heightened because of that.


May calls the fashion its own character in the film and notes that her role was part costume designer (who selects wardrobes to create a sense of character) and part fashion designer (who predicts trends). For her part, Heckerling is particularly excited that the clothes not only feel unique to each character, but that the overall palette changes to represent the seasons, moving from autumnal colors to Christmas reds and greens to Easter pastels. Shawn, meanwhile, calls the costumes “as fantastical as The Wizard of Oz.”

Like all good oral histories, this one bounces around a bit. It not only gets into the nitty gritty of creating the film’s explicitly feminine fashions but also explores how the film’s designer-obsessed high schoolers speak to a new generation of Instagram-loving teens. Plus Heckerling chats a bit about her upcoming musical adaptation of Clueless. And she reveals that she strongly considered Dave Chappelle for the role of Murray, but ultimately went with Donald Faison because Chappelle was too authentic for a character she wanted to be a bit of a poser.

But overall what’s most readily apparent is just how much all four interviewees still love this project. Shawn, in particular, is downright effusive, calling it “one of the greatest scripts ever.” He adds:

To be honest it was very forward looking, not just in the very believable friendships across races, but in the sort of very delightful way that the young gay boy is treated in the film and the respectful and charming way he’s treated. I think that 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.


Read the full, lengthy oral history over at Uproxx.

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