Did you think we could let the 20th anniversary of the release of Clueless slip by without us getting obsessive over the iconic costumes? As if! Did you think we could go more than one sentence without employing the film's most memorable catchphrase? Way harsh, Tai.
Okay, now that we've gotten that out of our systems, let's talk all things Cher, Dionne and Tai. Specifically, let's talk about their eye-popping costumes rendered by costume designer Mona May. Because any time a story decides to make points about class, sex and race—as Clueless does, in ways both subtle and overt—it's hard not to search for meaning in the visuals (although hopefully it’s less useless than searching for it in a Pauly Shore movie).
Clueless’ costumes alone make it clear why it’s become a generational classic for so many. May did a wonderful job of picking up on the current trends in teenage-wear (mainly by watching a lot of ‘90s music videos, it would seem). But her real brilliance was in how she interpreted those trends and how, by making the costumes of the film so memorable, she actually invented new ones. Even more impressive? So many of the outfits in this film still look current 20 years later. Or, at the very least, they’re not nearly as cringeworthy as they normally would be. It’s an almost-impossible feat for a costume designer to evoke current trends, set new trends and create an iconically classic cinematic wardrobe, but May managed it with flying colors (so to speak).
We couldn't possibly cover every costume in the film. Alicia Silverstone’s Cher Horowitz has 60-plus costume changes and manages to sport no less than six different ensembles in the film's first 90 seconds. No, for our own sanity, we'll be sticking to the iconic looks—like Cher's yellow schoolgirl plaid.
How do we know this is an iconic film costume? Because if you mention "Cher's yellow plaid schoolgirl outfit" to anyone who has ever seen this film, they'll know exactly what you're talking about. And because if you Google "Clueless halloween costume" you get a pretty decent version of this look available from Party City.
Note how this look works through several scenes and interactions. It plays off the glass of orange juice she offers in her first scene with her father, a moment that defines their affectionate but argumentative relationship. It definitely plays off Dionne's look, which is only a slight variation on it.
Dionne will go one of two ways in most of her costumes. This is the first way: a variation on whatever Cher's wearing in the same scene. In these instances, it's a way of establishing their bond as friends as well as their shared values. With these plaid looks (a motif Cher practically owns throughout the film, in at least a dozen costumes), it's also a way of establishing the influence Cher and Dionne have over many of the other girls in the school. When you scan background characters in large scenes, you'll see knockoff versions of these and other noticeable Cher and Dionne costumes.
When she gets to class, she sheds the jacket in order to highlight the baby sweater she's wearing underneath. Undersized layered tops were a trend through the nineties, but it's a particularly strong motif in a lot of Cher's costumes, as a way to underscore her naivete and childlike nature. In this scene, in which she plays with her gum while talking about partying with the Hait-ee-ans, it's a particularly good way of showing her immaturity.