More than 30 years on, the hit Hollywood teen comedy Clueless is remembered for more than just Alicia Silverstone’s sparky performance as the popular and kind-hearted Los Angeles high school student Cher Horowitz. The 1995 film changed how teenagers were dressed on screen.

While the teens in earlier films like The Breakfast Club and Pretty in Pink wore clothes similar to what they’d wear in real life, costume designer Mona May realised the grunge fashion that had swept through schools wouldn’t be right for the technicolour world of Cher, her best friend Dionne and their posse.

“I had to invent the fashion because what was on the ground was grunge, so there was no blueprint. I had to really create this new world that these girls exist in that was very high-fashion but appropriate for high school,” she says.

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Figuring the two fashion-obsessed teens would pore over the runways of Paris and Milan, May took inspiration from European designers.

Cher’s most famous outfit – a Dolce & Gabbana yellow plaid suit with a white T-shirt, yellow cardigan and Mary Jane shoes – is iconic. As is the matching black-and-white version made for Dionne, which was styled with a “Dr Seuss”-inspired hat.

“It was about taking the runway looks and then translating them … Like, the first yellow suit she wears: I always think, ‘OK, high fashion, but then what would be the grounding factor? Catholic girls’ school uniform, right?’ That skirt or sweater vest, but then translated into Cher and on steroids,” she says.

Clueless, a coming-of-age comedy loosely adapted from Jane Austen’s Emma, has become part of American fashion history – although, ironically, writer-director Amy Heckerling’s main directive to May was that she wanted the fashion to “feel European”.

Its approach to teen fashion – putting fantasy above realism – can still be seen in contemporary shows like Gossip Girl and Euphoria.

May and Heckerling, who had already had hits with Fast Times at Ridgemont High and Look Who’s Talking, visited Los Angeles schools to research Clueless.

The pair’s distaste for what they saw is mirrored in the film’s protagonist, Cher Horowitz, and her diatribe against the sartorial choices of the opposite sex:

“I don’t want to be a traitor to my generation and all, but I don’t get how guys dress today. I mean, come on: it looks like they just fell out of bed and put on some baggy pants and take their greasy hair – ew – and cover it up with a backwards cap and, like, we’re expected to swoon? I don’t think so.”

Flanked by past designs, May is speaking on Zoom from her home in Los Angeles, where she has spent most of her adult life after a transient childhood that spanned India, Poland, Germany and New York.

I’d donned a black-and-yellow checked vintage Emanuel Ungaro jacket to interview May – a little ode to Cher’s iconic schoolgirl outfit. May’s eyes light up the instant she spots it and she insists I stand up and give her a twirl over Zoom.

As teenagers in the 2010s, obsessed with anything from the 1990s, a friend and I recreated Cher and Dionne’s matching plaid looks for a high school party (sadly, I no longer own the costume).

‘Are they rich or poor? Are they depressed? Are they happy? Are they oversexed or undersexed? That is beautiful, and that’s why I’m so passionate about my job – because I get to really do this in a very nuanced way.’

Mona May, Clueless costume designer

Despite discussing the fashion of Clueless for the past 30 years, May’s passion for the subject has never waned.

“When you think of a character coming onto the screen, you don’t have to say a lot, but in 10 seconds you know exactly who they are [from what they’re wearing],” she says.

“Are they rich or poor? Are they depressed? Are they happy? Are they oversexed or undersexed? That is beautiful, and that’s why I’m so passionate about my job – because I get to really do this in a very nuanced way.”

One moment that truly encapsulates fashion’s capacity for storytelling is in the film’s third act. Having failed her driver’s test and listened to her friend Tai (Brittany Murphy) confess her affection for her step-brother, Cher is set adrift and confused through the streets of Beverly Hills, all to the tune of Eric Carmen’s All by Myself.

“In that moment she’s lost … she was always in control of everything, and her outfits were tailored, perfect and matched. And in this outfit there’s a shirt made out of a wrinkly material, which is a silk chiffon … it’s layered in a way that’s almost sloppy,” May explains.

Similarly, the wardrobe of Murphy’s Tai – the scrappy, wide-eyed teen who Cher takes under her wing – follows a similar arc, from grungy flannels to Cher clone, to a happy medium between the two.

In contrast to the main characters’ upper-class sensibilities, May’s budget of $US200,000 to create about 60 outfits for Cher, 50 for Dionne, and hundreds more for the rest of the cast meant she couldn’t afford to rely solely on designer labels.

This was a time before fashion labels and their PR teams hounded film and TV executives to have their designs worn on screen.

Cher’s red Alaia dress, memorable for her outcry, “You don’t understand. This, this is an Alaia!” while being robbed at gunpoint, was borrowed from the brand’s Paris Atelier.

Meanwhile, her white “Calvin Klein” slip dress was actually made by the lesser-known designer Anna Sui.

The rest of the costumes came from shopping centres and op shops.

Celebrating its 30th anniversary this year, Clueless’ influence continues to echo today: Iggy Azalea and Charli XCX channelled the look in the Fancy music video; Harry Styles wore a plaid Gucci blazer at the 2021 Grammy Awards; Taylor Swift wore a yellow plaid ensemble by Dior at the 2024 MTV Video Music Awards.

Cher’s computerised wardrobe – a work of fiction at the time that drew the envy of teen girls worldwide – is now a reality thanks to AI-powered apps.

In April, Alicia Silverstone revealed she would reprise her role as Cher in a spin-off series (May has not said if she will be working on the project as costume designer).

Having recently attended anniversary screenings of the film, she’s been delighted to see fans young and old – including an eight-year-old girl dressed in a plaid two-piece – continue to connect with her work. This is no small feat, she notes, given how “sophisticated” and discerning today’s youth can be.

“I would say I’m, like, the first influencer in the world. And without Instagram,” she says.

To commemorate the film’s anniversary May has penned a book, The Fashion of Clueless, which features behind-the-scenes anecdotes, juicy details for fashion lovers, and interviews with cast members including Alicia Silverstone, Stacey Dash and Paul Rudd.

‘I would say I’m, like, the first influencer in the world. And without Instagram.’

Mona May

While Clueless may be May’s most-talked-about work, the costume designer is the brains behind many other well-known films from the late ’90s and 2000s, including The Wedding Singer, Romy and Michele’s High School Reunion, Never Been Kissed, The House Bunny, Ella Enchanted and Stuart Little 2.

“When you see movies that I design, there’s a signature, there’s a colour, there’s a humour,” she says.

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But costume design, she says, is about more than just visuals. For most actors involved, Clueless was their first major role. Many were – excuse the pun – rather clueless about fashion, and it was May’s job to counsel them in the confidence and comportment needed to wear the clothes believably.

“Alicia [Silverstone] at the time was very young [18] and she was running around with clogs and sweatpants. She wasn’t used to these kinds of clothes. So in the fittings she learned how to wear them,” says May.

Barely older than most of the actors themselves, May says the set’s spirit was one of experimentation and excitement.

“Amy [Heckerling] was always there as our big old mother hen … we were like kids in the playground, we were having so much fun.”

Silverstone still texts May for fashion advice, while Drew Barrymore, with whom May has worked on several projects, remains a close friend.

“We all are quite insecure as humans and I think that’s when you have the relationship for a very long time [referring to Silverstone and Barrymore], they rely on you. You have a shortcut of understanding and trust.”

The Fashion of Clueless is out now via Simon & Schuster.