Few pop-culture gemstones have had as much of an impact on fashion as Clueless, the ’90s rom-com that celebrates an anniversary this week amid a next-gen revival. Mona May, the film’s costume designer, is one of the most prolific talents in the industry, deserving of credit for our modern worlds. May’s styling for pre-Y2K cult hits like Romy and Michele’s High School Reunion and Never Been Kissed has shaped 2021’s fashion (Liquid minidresses! Twinsets!), while Clueless’s Cher (Alicia Silverstone) and Dionne (Stacey Dash) remain lifestyle muses decades later. “It’s not just the fashion that mesmerizes people over the 25 years since the movie has been out,” May tells me on a video call from Berlin. “Each look really was related to who they were. You love these characters—you love the girls.”

In 1994, once Amy Heckerling wrote the film and tapped May to style it (the two met like “twins who found each other” on a pilot that never aired), they looked forward. “This is really a movie about fashion in the future,” says May. “At the time, everyone was really dressed up or underdressed,” she says of remixing this on film. “What I introduced was thrift-store clothes with high-fashion clothes with clothes from the mall—something that now is such a normal thing to do. You know, we wear the Balenciaga purse with ripped jeans and flip-flops.”

She imagined Cher and Dionne as Beverly Hills teens who, like May, traveled globally and went to Paris shows to scout then came home to think of something new. “It’s interesting, with Silverstone, we actually had to teach her a little bit more how to wear designer clothes because she was just a kid, a hippie animal activist already,” remembers May. “And then you have Stacey Dash, who already knew about fashion, and she drove certain things and wanted certain things—how they should fit, how they should look on her.” Seeing it now, “that’s part of the charm and also why women relate to these characters,” May shares. “Cher was herself in one way different from Dionne, who’s more funky and outrageous.”

As I write, I’m wearing one of my most faithful ensembles, a white tee layered with a black tank and bike shorts—not far from what May dreamed up as a high school’s monochromatic P.E. dress code. “Everyone had their own specific style,” May explains. “When you look at Cher, she has the white T-shirt that’s now so synonymous with the black tank—which now everybody wears! My P.A. just came to work wearing it, and I said ‘You know, that’s what Cher wore in gym,’ and she was like, ‘Oh, I didn’t see Clueless yet!’” May says with a laugh.

“It’s so funny how it’s now in our zeitgeist, it’s just part of our fashion,” she admits. “The whole movie was an inspiring riff on something.” For Vogue, May riffs again, reimagining her Clueless muses via 2021’s shoppable lens:

Cher’s Morning Routine at Home

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“Cher always had the latest technology,” says May of incorporating things like cell phones, beepers, and wardrobe-matching programs into the film. “In 2021, Cher has an iMac with all her clothes digitally on file—it has to be pink,” says May. “She wakes up and starts her day with a cup of tea, and of course she coordinates her outfits to find the perfect match.”


“Cher knows trends,” May points out of Telfar’s just-launched Ugg collab. “She had to have her fluffy slippers around the house. At home, Cher always wants to be comfortable yet stylish.”

“I chose this because throughout the movie you see Cher at home and she still is so well put together,” May points out. “The shorts are a perfect replacement for miniskirts; it’s always beautiful weather in Beverly Hills, so shorts are the best way to go

Cher and Dionne’s First Day Back

How Cher and Dionne Would Dress in 2021 According to the Costume Designer of Clueless

Cher and Dionne at Gym

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Dionne Goes Shopping

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Cher and Dionne at a House Party

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