Costume Designer Mona May Talks the Iconic Wardrobe

In July 1995, Women’s Wear Daily declared Amy Heckerling’s hit rom-com “Clueless” as “the fashion movie of the year.” Three decades later, the movie’s costume designer Mona May revisited one of the crown jewels of her career in a conversation with WWD. “It’s an incredible feeling for any artist when their work is relevant and people love it,” she said.

The clothes May curated for Beverly Hills teen Cher Horowitz (Alicia Silverstone) and her posse are still deeply coveted, with some of Cher’s famous looks including her bright yellow plaid Jean Paul Gaultier skirt and blazer set, her red Alaïa party dress and her white Calvin Klein “underwear” dress. These ensembles and more are detailed in May’s upcoming book, “The Fashion of Clueless,” a behind-the-scenes look at her costuming process, set for release later this year. The cover art? Yellow plaid.

“It’s really incredible that when it came out, people started dressing like Cher and Dionne and all the kids. And now the new kids who are like 16, who were not even born when the movie came out, are loving it,” the costume designer said.

In just the past few years alone, “Clueless” has inspired a 2022 Crocs collection and a 2023 Super Bowl commercial. In 2025, L’Ermitage Beverly Hills and Bloomingdale’s Century City are celebrating the movie’s 30th anniversary in addition to The RealReal, which tapped May to curate an edit for the milestone.

So, how exactly did May create such enduring fashion? She wasn’t inspired by the homogenous clothes worn by actual high schoolers of the time, which she described as “horrible.” May, who was born in India and raised in her mother’s and father’s respective countries of Germany and Poland, looked instead to Europe for inspiration.

“Think of the famous actresses of the ‘50s, Audrey Hepburn. That kind of style really appeals to me, that to me is very timeless,” she said. “It’s a twin set that you can wear in the 1950s — you can wear it now. I think of the A-line skirts, pea coats, berets.” May also emphasized that these classic silhouettes are reliable and “female-friendly.”

May also poured over runway looks for inspiration. While luxury designer names are peppered throughout the dialogue of “Clueless,” she emphasized that she was working on a limited budget — in fact, major studios were resistant at the time to films that focused on female stories.

“They were like, ‘You need to put more boys in there,’” she said of the reaction to Heckerling’s “brilliant script,” which is adapted from Jane Austen’s “Emma.”

The film eventually found its home at Paramount, and Heckerling allowed May the creative freedom to explore, adding flair to ensembles with quirky hats, bold colors and knee socks. As for the tight budget, May had to be thrifty — she used several designer looks but also visited thrift stores and malls to round out her wardrobe, and it was precise tailoring that elevated these garments to look couture.

“In the fitting, that’s where the chemistry happens. It’s almost like a laboratory for a costume designer,” she shared. “That’s where everything really jives, because then you have the actor, you have the director, you have me myself, and we can put the clothes on the body and really then see what happens. And that’s a very magical time for actors, because that’s when they really get the information of who they are as the character.”

For Cher’s first day of school, May had several plaid outfits for Silverstone to try on, including blue, red and yellow. The blue was missing a certain “power”; the red had a premature Christmas feeling. And the yellow?

“We all had almost like goosebumps in the fitting room. It was so perfect. She loved it herself. She felt very uplifted in that color, in that look. And it was so classic,” May said. “The yellow worked with her blond hair, with her skin tone, and it was just the ray of sunshine that we needed for that exact scene of being in a quad, first day of school, queen bee.”

Costuming details continued to reflect the characters’ progress in their story arc. When Cher concludes that she is “totally clueless” as she despondently wanders town and then figures out that she loves Josh (Paul Rudd), she’s wearing a pale blue and white ensemble including an argyle skirt and sweater vest underneath a sheer ruffly top.

“There was something soft about it,” May said of the look. “She had a barrier with all the tailored stuff — the barrier was kind of gone, like she was breaking down. So I think that the chiffon worked really, really well, I think the color worked well.”

Unlike the quest for the out-of-budget Alaïa dress, which was requested to be borrowed, not every outfit required extensive sourcing.

Of Paul Rudd, she said, “He really was the guy that he played — in jeans, in plaid shirts, in T-shirts. We used a bunch of his clothes that he wore. I think he wore his own boots the whole time, and some of his plaid shirts. We were talking to him for my book, and he was like ‘Remember, Mona, I brought all that stuff?’”

May also recalled the late Brittany Murphy, who plays Cher’s new-in-town makeover target Tai, and the way she approached wardrobe: “What was so cool, too, with Brittany, even though she was 17, very young, she was very smart about creating this character. When we first met, she said, ‘Mona, I want to make sure that I don’t look great when I show up at the school. Don’t make me look good.’ And we really went for it, kind of what everybody actually wore at the time, the grunge look. So there was a place to grow from there.”

May has had several “pinch-me” moments since “Clueless” became embedded in the fabric of modern pop culture, from Kim Kardashian dressing up as Cher for Halloween in 2023 to Iggy Azalea recreating scenes for her massive hit 2014 music video, “Fancy.” And she credits “Clueless” as propelling the rest of her vibrant career, which includes costume designing for beloved movies like “Romy and Michelle’s High School Reunion” and Disney’s “Enchanted.”

At the heart of May’s work is a passion for storytelling through fashion, and 30 years later, the love she poured into “Clueless” is still palpable in every stitch. Mona May is certainly one woman who is neither “fashion victim” nor “ensembly challenged.”