Although we often credit today’s algorithm-driven culture with elevating the “rich-girl” aesthetic, its blueprint was quietly curated in part back in 1995. Now, as Amy Heckerling’s Clueless turns 30 this summer, its wardrobe still reads like the original style bible: white tees layered under spaghetti-strap tank tops, twin sets, peacoats, and preppy school prints—most memorably that yellow-checked blazer-and-skirt combo.
In Clueless’s Beverly Hills, Cher didn’t need Instagram to broadcast—nor was it invented yet—she simply stepped out of her Jeep in head-to-toe plaid and let costume designer Mona May’s vision of a “Catholic school uniform on steroids” do the talking. That canary-yellow blazer and micro-pleated mini by Jean-Paul Gaultier—not to mention her entire meticulously catalogued wardrobe pulled from designer boutiques like Fred Segal, and “funky vintage shops on Melrose”—stands as one of the film’s most enduring and influential elements.
Presented as a campier, more lighthearted alternative to the TV series Beverly Hills, 90210, Heckerling uniquely presents high school world-building and a satire on class, wealth, and romance through a teenage group that often wears designer suits and skips gym class with “doctor’s notes” from plastic surgeons. Fast-forward to today, and searches for “Clueless outfit ideas,” “90s fashion revival,” and “rich girl aesthetic” have spiked on Google, proof that the aspirational fantasy still largely resonates.
Clueless (1995), written and directed by Amy Heckerling. From left: Alicia Silverstone as Cher Horowitz and Stacey Dash as Dionne Davenport.
The movie’s maximalist fashion has also influenced designers for decades. Designer Jeremy Scott, Moschino’s creative director from 2013 to 2023, reminds us that Clueless’s costumes were, in fact, some of the best supporting actors. “They were another character in the film,” he says, underscoring how a few memorable looks can anchor an entire cultural moment. “That [plaid] suit is the thing that most comes to mind when I think of the movie,” he adds, crediting May’s creations for remaining in the zeitgeist long after the credits rolled.
For his Moschino Spring 2022 “Baby Lady” collection, Scott channeled Clueless’s playful preppy spirit.
That [plaid] suit is the thing that most comes to mind when I think of the movie.
Jeremy Scott, Designer
Scott’s own Moschino Spring 2022 “Baby Lady” collection felt like Cher and her fictional contemporaries' closets crashing the runway: pastel midriff-bearing skirt suits, oversized gingham prints, and even stuffed-animal details on cocktail-ready gowns. Models toted giant baby-bottle handbags down the runway—a cheeky wink to youthful innocence that could’ve been plucked straight from Dionne’s closet. Scott confesses, “I definitely took notes for that season” when dreaming up the collection.
The film’s sartorial influence doesn’t end there. Even Harry Styles’s plaid Gucci blazer at the 2021 Grammys received Alicia Silverstone’s approval—“Cher would be so honored (and totally approve!!),” she tweeted—while Maria Grazia Chiuri’s tartan-heavy Dior Pre-Fall 2022 collection paid homage to the school-yard, with Natalie Portman as a spokesperson. She wore a head-to-toe tartan look during her Thor press junket, reminiscent of Horowitz’s Gaultier plaid.
And beyond the clothes themselves, Clueless gifted cinema some of fashion’s most quoted one-liners. Cher’s Alaïa shout-out—“that’s like, a totally important designer”—became a quick lesson in fashion with one impeccably delivered line to a thief at the Circus Liquor parking lot in North Hollywood.
Her infamous “Calvin Klein!” retort to her father Mel’s “Says who?”—itself the capstone of the now-iconic exchange (“What the hell is that?” “A dress!” “Says who?” “Calvin Klein!”)—was a spontaneous addition to the script, according to May, and it cemented the slip dress (and Silverstone’s oblivious delivery) in pop culture so thoroughly, that creative director Francisco Costa recreated it in a 2010 collaboration with the now-closed L.A.-based boutique Confederacy.
Presented as a campier, more lighthearted alternative to the TV series Beverly Hills, 90210, Heckerling uniquely presents high school world-building and a satire on class, wealth, and romance.
Even the film’s quirkiest accessories—campy hats, some sourced from Kokin, a local New York milliner; thigh-high stockings; Versace white patent leather bow mules; and Manolo Blahnik's black satin feather-trim slides—have become enduring style icons. “It’s playful, it’s colorful, it’s generally joyful. It’s a little over the top,” Scott reflects. Of course, with much of its '90s-era fashion currently cycling back into vogue, the style of Clueless is ripe for a renaissance—especially among Gen Zers, many of whom are discovering the film for the first time.
Clueless’s 30th-anniversary re-release (and May’s upcoming book, The Fashion of Clueless) reminds us why the film holds a rare place in the annals of teen cinema. The film fashion remains timeless, fun, and a sartorial masterclass. So, really, should we ever stop taking notes? As if!
