Costume designer Mona May digs deep into the wardrobe to reveal some secrets about the film’s iconic looks
As any disco-dancing, Oscar Wilde-reading, Streisand ticket-holding friend of Dorothy knows, Clueless is peerless in how it mainlined high fashion to its audience. Cher in her canary tweeds, Tai in her stoner plaid loungewear, Amber in her Cruella meets Claire’s Accessories marabou feathers – every character had their own unique look. The film’s sartorial swagger has since been borrowed by everyone from Karl Lagerfeld (who pilfered the idea of a Chanel water bottle holder for his AW94 collection) to Charli XCX and Iggy Azalea.
Nearing it’s 20th birthday, Clueless and its memorable outfits are just as aspirational as they were when we were all virgins who couldn’t drive. Mona May, the ineffable costume designer behind each character’s dress (literally, she dressed every single person who appears in the film), divulges what it took to construct a look that is often imitated, never duplicated.
SCORING AN ALAÏA DRESS WAS A MAJOR COUP
“To get an Alaïa dress I had to make so many calls. There was really no club promoting at the time, there was none of what’s happening now; it was really all my footwork, trying to bring these designers in. And my budget wasn’t huge, so (we used) whatever I could get for free, and Alaïa was very generous with the pieces – he was such a collaborative designer.”
DIONNE HAD TO LOOK SEXUALLY FORWARD TO CONTRAST WITH CHER’S INNOCENCE
“Dionne is sassy and a little bit more experienced. Cher was very innocent and classic; Dionne was very sexually forward. With her I took designer clothes from the runway and mixed it with vintage fashion, so we would have, let’s say a Dolce & Gabbana top that goes with a vinyl skirt that’s super short and then we’ll add a 1950s clutch to it, but on top of it we would add a funky, crazy hat and really make it work. We wanted to make sure she didn’t look like a clown. We could push the envelope with her on every level.”
THE FILM’S BACKGROUND WAS BLAND TO MAKE THE COLOURS OF THE CLOTHING POP
“The production designer was like, ‘Let’s go for greys and neutrals to make the costumes pop more.’ We discussed early on with Amy (Heckerling) that the costumes need to talk. We didn’t use much black, grey and stuff. It was up to the production designer to have all the sets very muted, very grey, very neutral palette. Everything the girls wear pops out and doesn’t clash with the things behind, so it was like a clean canvas for us.”

THE GUYS’ BAGGY JEANS WERE DESIGNER
“Guys are guys and they were very much into baggy pants and plaid, all that hideous stuff that was going on in California high schools when we were scouting. I wanted to elevate it, so I put them in the designer jeans of the time. Then you had Murray’s clique who wore Sean John – cool ‘hipster’ clothes you would call them now. We had to be careful because they should never look like a gang member. Murray had to look well with Dionne – she would never date a guy who did not know about fashion, aesthetically she shopped for him too.”
CHRISTIAN’S LOOK WAS TAKEN FROM THE RAT PACK
“For Christian, Amy had the idea of the Rat Pack, it really came back to being a little bit out of the norm. You didn’t have this kind of metrosexual look that we have now, so it was like, ‘OK, how do we make him different from all the guys?’ But we don’t wanna sell the idea that he’s gay, because that has to come out in the script. So we were thinking in the terms of very, very vintage. The pants that he wore were 1940s pants, the jacket was a 1940s jacket. It was about working with the proportion for him so he looks modern; he doesn’t look like a mannequin walking around in period clothes.”
ONE OF CHER’S DRESSES NEVER MADE IT INTO THE FILM
“A lot of the time you have such great ideas on the page, but once you get in the fitting room and you start putting the clothes on, something that seemed so fabulous would really start to not work on the actress because of her shape or colour or it wasn’t really the character. There was this beautiful dress that I was agonising over. I thought it was perfect, and we put it on and just went ‘No!’ It’s too sexy or it’s too slutty or it doesn’t fit on your body or it’s just not like Cher.”
DIONNE’S WEIRD SPIRAL HAT WAS A MIRACLE FIND
“That was a crazy find. I don’t even know who designed that hat. It was secondhand from some crazy hat store from some random lady in some random, random little boutique and as soon as I saw it, it was one of those ‘Oh my God, this hat is perfect! How are we gonna make this work?’ It’s always about achieving the balance with Dionne; how far can we push it without crossing the line? With this hat I think we almost did (cross the line) but we made it work.”

What R&B bangers would Dionne’s dress-up playlist have included back in 1995? Have a listen below: