Clueless costume designer Mona May: ‘I couldn’t take style inspiration from Nineties teens so I had to invent Cher Horowitz’s look’

It’s not often that clothes become so woven into the fabric of a film that a script is edited specifically in order to make reference to them. But when costume designer Mona May secured a scarlet Azzedine Alaïa dress for 1995 teen comedy Clueless, she phoned up screenwriter Amy Heckerling to ask her that she do so. “I said, I’ve found this Alaïa dress, can we write that in the script?” May tells me over zoom from her Los Angeles home.

The resulting line became one of the film’s most memorable, as Beverly Hills teen Cher Horowitz is held up at gunpoint and her assailant insists she lie on the floor of a petrol station while he makes his escape. “You don’t understand, this is an Alaïa!” Cher protests. “I had to tell the designer, ‘I just want you to know, she’s going to be on the ground.’” May says. “We were basically cleaning the floor that she was lying on in the scene to make sure we didn't damage the dress.”

This October marks 25 years since the film’s UK release. During the two decades since, Clueless, starring Alicia Silverstone, Brittany Murphy and Paul Rudd, has become a cult classic. The modern reimagining of Jane Austen’s 1815 comedy of manners Emma follows the privileged high school existence of Cher (Silverstone) and her best friend Dionne (Stacey Dash) and has become as recognisable for its Nineties clothing as it has for its cutting and endlessly quotable one-liners.

But, much as we have grown to associate Cher’s tartan yellow Dolce and Gabbana skirt suit with being the archetypal aesthetic of the decade, it wasn’t actually what the teenagers of Beverly Hills were wearing at the time. Instead, most of them were dressing far more like Tai (Murphy) in the Kurt Cobain-inspired grunge trends of the moment than they were like Cher or Dion, explains May.

“Amy Heckerling really wanted the film to be ultra-feminine, very pretty, a kind of antidote to what was really happening on the street,” May tells me from her suitably colourful home, stacks of magazines and high heels piled up behind her. “We wanted to change the trends and give permission to women to be girly. I couldn’t take that from what the teens were wearing, so I had to truly invent it.”

May designed the costumes for some of the most famous fashion films of the era, such as 1997’s Romy and Michele’s High School Reunion, 1998’s The Wedding Singer and 1999’s Never Been Kissed. But it was Clueless that proved the most enduring when it came to fashion. In many ways, that’s down to circumstance. The teen comedy was one of May’s first feature films and was produced under strict time and budgetary constraints. She was only given eight weeks to pull together a roster of uber stylish costumes, including more than 60 different outfit changes for Silverstone alone.

With limited access to couture and little inspiration to be taken from the teens of the day, May looked both to her international roots (she was born in India to a German mother and grew up in Poland) and the past, for inspiration. These influences run throughout Clueless, from Catholic school girl-inspired kilts and vintage plaid to French berets and turned up cuffs. “I couldn’t afford to buy much designer, and this was pre-PR firms lending the actors clothes, so I really had to be very innovative and inventive in what way I could create this world with not a lot of money,” she says.

“These girls were so wealthy that they themselves probably went to the runway shows and were able to really choose whatever they wanted, write down number one outfit, number five outfit, the number six outfit, that they want to purchase,” May explains. “I had to think, how would they take items from the runways and really make it fit their world?”

The resultant aesthetic May engineered was a mixture of designer and vintage. Of course, clashing high and low fashion through combining vintage with the new is commonplace now, thanks to increasing concern among the younger generation for the damaging impact fashion has on the environment, but twenty-five years ago, it was quite innovative. 

Today, vintage shopping sites like Depop, Rebag and Vestiaire Collective often throw up Nineties items, seeing a huge revival in the decade’s trends. Teens on video sharing app TikTok now recreate outfits from Clueless using items from their own wardrobes. “I have younger friends who are like, ‘Oh my god, do you know that you’ve gone crazy on TikTok’,” May laughs.

I ask May why she thinks the younger generation are so intrigued with our very recent past, especially given many weren’t born when Clueless was first released. “You know, maybe because of the times we’re in now and that intensity we are going through, it’s nice to look back to the more innocent times,” she says. “That’s not to say Clueless is without substance, they are deep girls, but I think there’s a little bit of that nostalgia for those times without cell phones and knowing everything that is happening everywhere in the world. Life wasn’t that complicated to the teens back then. There's a lot more that young people have to deal with now. ”

 It’s this factor which makes May somewhat apprehensive about the upcoming Clueless reboot. Written by Will and Grace writers Jordan Reddout and Gus Hickey, the film will be reimagined as a mystery TV series in which Cher disappears and Dionne goes out in search for her. It’ll be set in the modern day and has the questionable working tagline of “Mean Girls meets Riverdale meets a Lizzo music video”.

“I hope that they can write something that really can be meaningful and powerful and the essence of these girls. Sometimes things don’t really pan out so well with reboots, but you never know.” Whether a Clueless reboot can match the enduring might of the original, only time will tell. What is clear is that it will be a tall order for the costume designer to meet the enduring appeal of the 1995 original.

Clueless is available to watch now on streaming service NOW TV. You can follow Mona May on Instagram at @itsmonamay.