Clueless defines ’90s style for a new generation, three decades on | Canada Voices

Beverly Hills Mayor Sharona Nazarian officially declared July 19 as Clueless Day, honouring the 30th anniversary of the iconic film with a city-sanctioned celebration.

Loosely inspired by Jane Austen’s Emma, Clueless may wear the label of a rom-com, but at its core, it’s a love letter to female friendship and a testament to the transformative power of style. Its wardrobe continues to define 1990s fashion for a new generation of pop icons and trendsetters, from Taylor Swift to Harry Styles to Olivia Rodrigo.

“It was my first studio movie,” recalls L.A.-based costume designer Mona May. “Alicia had 63 costume changes. Dionne had about 45. Amber, Tai – same. And I had to dress all the extras too. That’s hundreds of looks. And we only had two months of prep,” she says, referring to Clueless stars Alicia Silverstone (Cher), Stacey Dash (Dionne), the late Brittany Murphy (Tai) and Elisa Donovan (Amber).

May says she’s never had that kind of challenge on the other films she’s worked on, including the equally iconic Romy and Michele’s High School Reunion. “My wardrobe budget on Clueless was $200,000,” she says, adding that this is less than the current price of a Dior couture dress and a movie’s catering budget at the time. She’s sharing more factoids in her new book The Fashion of Clueless, which hits shelves in October.

That tight budget didn’t cramp May’s vision, though. Instead, she championed a high-low mix of designer hits and mall must-haves at a time when grunge was in full swing.

“We did our research and everyone in L.A. high schools was wearing grunge – it was grey, shapeless, dark and depressing,” she says. “They needed to look like students, not models, so I decided I had to make grunge look less dude-like and stop the girls from looking sad.”

“People always say we glamorized grunge. And we did,” adds May about resetting the bro aesthetics that Nirvana made popular. “We took the plaid, the boots, the layered looks but made them polished and made them pop.”

May also went to the popular L.A. gay club The Abbey and took inspiration from drag and nightlife culture. “That playful energy was a huge influence on the film and, of course, with Romy and Michele.”

Clueless laid the kaleidoscope and multicoloured groundwork for Sex and the City and Legally Blonde and even for the Versace fall 2018 runway collection. “To see Donatella [Versace] do a collection inspired by Clueless was like being blessed by a goddess. I studied Versace at design school so it was mind-blowing,” May says.

Nowhere is May’s joyfully subversive vision clearer than in Cher Horowitz’s yellow Gaultier plaid skirt suit. “It was a total accident,” May admits. “I tried a blue and red jacket and skirt first. Then I saw the Gaultier suit hanging at Barneys or Saks- I can’t even remember. We tried it on, and the director, Amy Heckerling, said, ‘That’s it.’ Alicia instantly became this ray of sunshine and the high school Queen Bee in that look. It also screamed confidence.”

That isn’t the only iconic style moment in the film. When Cher is mugged while wearing a clingy red party dress, she famously protests, “It’s an Alaïa!” – a line that gave designer Azzedine Alaïa a global stage beyond European runways.

“Other than fashion fans, so many people didn’t have a clue who he was until Clueless was released,” May says. Another standout: the white Calvin Klein slip dress, which was such a hit that the brand reissued it in 2010.

Among today’s style and pop culture enthusiasts, the cult film continues to captivate new generations. Harry Styles wore a Clueless-inspired plaid Gucci blazer at the 2021 Grammys (“Cher would be so honored,” Silverstone tweeted), and Jeremy Scott’s 2022 Moschino collection drew from the Clueless closet.

In 2024, Stoney Clover Lane launched totes, fanny packs and patches with quotes like “But this is Alaïa,” “Ugh” and “That was way harsh.” Rival doll companies, Barbie and Bratz, have recently both reimagined the Clueless cast in toy form.

But the film wasn’t just fashion-forward – it was a fashion narrative. “As a costume designer, you’re telling the story of who these girls are,” May says.

Cher’s empire waistlines and pastels amplified privilege and status. Dionne’s vinyl skirts and glam hats channelled punk meets prep. Amber’s chaotic ensembles screamed fashion victim chic. “Every outfit had intention.”

Clueless also broke teen movie tropes, casting characters who looked and dressed outside the mainstream. “We had Stacey Dash as a stylish Black girl, Tai as Asian-American, Christian [played by Justin Walker] as a fashionable gay teen,” May says. “That didn’t happen in teen movies. And it wasn’t a joke – it was aspirational.”

And the legacy continues. Mona May has reunited with Alicia Silverstone on a new British drama-thriller series, Irish Blood, premiering Aug. 11. “It’s fun to be back working together,” she says, noting the irony that Silverstone is vegan hippie who doesn’t obsess over clothes, yet Clueless made her a fashion icon.

When asked what Clueless would look like if it were made today, May reflects that it would look nothing like the flashy, fleshy styles prevalent on Love Island or The Bachelor. “Back then, we could tell a story through silhouette, colour, emotion and it was innocent. That’s why we had the knee socks and age-appropriate looks for the whole cast,” she says.

With the recent announcement that a Clueless reboot is in the works -reportedly written by Josh Schwartz and Stephanie Savage (of Gossip Girl and The O.C. fame) – May might find herself returning to the looks that launched her career, this time for Gen Alpha.

“Today, those old clothes might seem too ‘simple’ and with Instagram, too boring. But I think that’s why it’s timeless.”