As if it’s already been 30 years since Alicia Silverstone’s Cher Horowitz stepped onto our screens in her iconic canary yellow plaid skirt suit. Creating costumes so timeless that they continue to inspire runway collections, ad campaigns, and pop culture tributes decades later is no small feat — yet that’s exactly what costume designer Mona May achieved in 1995’s Clueless.

Eschewing the dominant ’90s youth fashion of grunge devotees and shredded denim, May crafted a sartorial sanctuary: a luxe, Rodeo Drive–inspired wardrobe, remarkably realised on a modest budget, that forged a fashion legacy and cultural anchor.

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Directed by Amy Heckerling and loosely based on Jane Austen’s Emma, the teen classic follows Cher Horowitz, who, as she famously says, ostensibly leads “a way normal life for a teenage girl.” Alongside her best friend Dionne (Stacey Dash), the film offers an irresistible glimpse into Cher’s glamorous, privileged Beverly Hills world.

The film’s ultra-feminine, polished aesthetic drew on the playful styles of the ’60s and ’70s — think sweater sets and plaid minis — as well as the influence of designers like Jean Paul Gaultier and Azzedine Alaïa (whom Cher famously calls “like, a totally important designer”). It served as a stylish counterpoint to the gritty streetwear dominating youth culture at the time. Perhaps it’s this contrast that continues to captivate audiences and keeps the film’s sartorial dreamscape so relevant today.

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In an early scene, Cher scrolls through her digitally archived wardrobe, filled with Calvin Klein slip dresses, plaid co-ords, and berets. The moment felt futuristic at the time and remains strikingly relevant today, foreshadowing the rise of virtual styling apps and curated digital wardrobes.

LA-based wardrobe designer Lisa Adams even recreated Cher’s system for her clients using smart mirrors and AI. Sharing the invention on Instagram, she captioned it: “Imagine a mirror that knows your wardrobe better than you do! Welcome to the next level of getting ready… think Clueless 2.0.”

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The outfits Cher selects, along with the many looks she wears throughout the film, feel as fresh and timeless in 2025 as ever, thanks in part to the ongoing ’90s revival. Her monochromatic P.E. outfit, for example, taps into three current trends: athleisure, layering, and ’90s nostalgia.

The tiny purse she carries on a shopping trip with Christian resembles a vintage prototype of the now-iconic mini Jacquemus Le Chiquito. And her trusty Mary Janes, a staple in nearly every outfit, have made a surprising comeback in 2025, evolving into hybrids seen across styles from Ugg boots to Salomon trainers.

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More than three decades on, Clueless’ influence remains palpable. Alexander Wang, a vocal fan of the film, sent argyle twinsets and ruffled blouses down the runway for his Spring 2014 collection. Cher’s signature marabou trim has appeared across diverse designers’ collections, from Roberto Cavalli to Simone Rocha.

Even Donatella Versace riffed on Cher’s first-day-of-school outfit for her Fall/Winter 2018 runway. Meanwhile, artists like Iggy Azalea and Charli XCX recreated iconic Clueless scenes in their 2014 hit music video “Fancy,” proving that Cher’s style remains a vibrant thread in pop culture’s fabric.