How ‘Clueless’ Started the ’90s Prep Renaissance—And Ended the Grunge Era of Fashion

Mona May lovingly scolds me on Zoom. “I want women to try different things and be silly characters—and not to be afraid to get out of black,” she is saying. “I’m talking about you, Meg!!” Soon enough, I am tasked with pulling out colorful items from my wardrobe for her discerning eye. “How about some nice greens on you?”

I should have known better than to attempt an understated black moment for an interview with a costume designer—especially this costume designer. May did, after all, single-handedly influence a generation of young women to go bright and bold with their clothes. The term “iconic” is often thrown around too freely, but when it comes to Mona May, it fits. She gave us the pink and blue minidresses of Romy and Michele’s High School Reunion; the whimsical Disney-fied ball gown of Enchanted; the all-white feather boa look in Never Been Kissed. And, of course, the delightfully preppy, fashion-forward world of Clueless.

May’s resumé is filled with beloved movies, but Clueless is perhaps her greatest triumph. The impact of her work on the 1995 film, which celebrates its 30th anniversary on July 19, can’t be overstated. The red Alaïa mini! The white Calvin Klein slip dress! The Jean Paul Gaultier yellow plaid skirt suit! These and so many other unforgettable looks from the film are part of fashion history.

The “Clueless look” quite literally redefined youth fashion of the ’90s, and it became a lasting symbol of teen culture. Re-creations of outfits from the film can be found everywhere, from recent teen films like Bottoms and Do Revenge!, to Iggy Azalea’s “Fancy” music video, to countless celebrity Halloween costumes.

Indeed, it’s hard to imagine a time when the visual world of Clueless didn’t exist—but, of course, it all came from the minds of May and the film’s writer and director, Amy Heckerling. 

While Cher, Dionne, and Tai may be the film’s three leading ladies, there is a fourth character who is just as important—and that is, of course, the fashion itself. “[The fashion] was very strong in the script,” May recalls of her first impressions of Clueless. “And I think partially why I got the job, too.” She had previously met Heckerling on a pilot that wasn’t picked up: “and we fell in love with each other, creatively, you know.” 

May was born in India and grew up in Warsaw. She went on to study fashion in Paris and New York before finding her way to the world of costume design. “That [experience] was something that [Heckerling] wanted to bring to the film, I think she wanted to bring that fashion—and to bring something that wasn’t so American,” May says. “I was just so excited, because truly, coming from fashion and loving costume design, there was such an opportunity for me to bring these two things together.”

From the start, May and Heckerling shared a vision. “It really was about the girls in high school who were rich, who had Daddy’s credit card, who go to fashion shows in London, Paris, and just have whatever they wanted. That was something that was very strong in the script,” May says. It was, in other words, a very different vision of teen fashion than what was happening in the real world, where grunge had been the universal teen uniform. Clueless was, she says, “not what was happening on the street in 1994.”

May wasn’t pulling directly from the catwalk, though. “If we just put them in runway fashions, it wouldn’t feel right. They would look like snooty models—you really wouldn’t know who they are,” she explains. “It was very important that they feel youthful and real and authentic. So, I had to take the fashion from the runways and then translate it into the high school setting.” 

Clueless is peppered with classic prep school pieces—Mary Janes, over-the-knee socks, A-line pleated skirts, frilly tops—a kind of “Catholic school girl but make it high fashion” approach. In addition to looking at contemporary runways and academic uniforms, May also sought inspiration from the Austen novel that inspired the film, Emma.

“It was important to look at Emma. What I got from the period that Emma was written in was the femininity that was also really important to bring into our film,” she says. “That was something that Amy was very adamant about, too.” Thus, Clueless nods to the Regency era with its fashion, too: a little cap sleeve here, a subtle empire waist there. “I really always like to work with pieces that are feminine,” she goes on. “I always love a little twin set, a little peacoat, a little beret.”

Out of this mish-mash of inspiration comes the iconic Clueless looks we know and love today—and perhaps the best example is the iconic yellow suit. “If you look at the classic Catholic school uniform, you have the plaid skirt with the little sweater vest, right?” says May. “So, we thought, ‘How would we now do that in our own crazy, cool world—on fashion steroids?’ And you get the Jean Paul Gaultier yellow suit.”

Incidentally, May tried a few other primary colors on Silverstone before settling on the now-famous canary yellow. The blue was “nice,” the red was “Christmas-y,” but the yellow? “It was like this moment! She became this ray of sunshine!” recalls May. “I like to talk about color and energy, and it really was like, ‘This is it!’ I mean, she is the sun ray of the school.”

But perhaps what is so brilliant about May’s vision for Cher is that she dresses like a real teenage girl. When she’s not parading around in an outfit put together on her ahead-of-its-time computer program, she’s relaxing at home. Maybe she’s wearing a white t-shirt under a pink vest with a scrunchie in her hair, or perhaps a big set of pjs. “I really loved that,” May says. “It was very important to try to ground the characters—to not make them fashion victims in any way.”

Today, this delicate balance of femininity, youth, playfulness, and designer fashion seems like the obvious approach for a fashion-forward teen flick—but at the time, it was revolutionary. In fact, some of the actors initially struggled to embrace May’s radical vision. Amongst the skeptics was the star herself, Alicia Silverstone. “When she got the part, I don’t think she really understood what it was going to be—that the fashion was going to be such a big part of it,” May says. “She was already an activist, just running around in her sweatpants with the dogs. It was interesting in the fittings—she was almost sometimes annoyed by having to try on all the clothes.” 

However, as time passed, learning about the clothes and understanding them helped Silverstone create the Cher we all know and love today. “The process of being in the fitting room was really important because you learn about the character. You’re starting to put the shoes on, you’re starting to put the clothes on, and, more and more, you start becoming the character,” she says. “And it was, I think, the same for Alicia. She began to learn how to carry herself and move with confidence. I think it was a process of her learning about the character through the fittings.”

Stacey Dash, who played Dionne, could not have been more different in her approach. “She already knew fashion. She came into the fitting room and she already had the style, she already had the groove, she already knew how to wear the clothes,” May recalls with a smile. 

Then there was Brittany Murphy, who played Tai. She, too, had a unique approach to her character’s clothing. “She was such a wonderful human being—and a very, very attuned person,” May says. “She was like, ‘Mona, I want to really be grunge. I don’t want to be pretty. Make me really baggy, so there’s room for us to play from there.'” 

May lights up as she starts talking about Tai’s makeover. “I love makeovers in films!” she exclaims. “It’s something that we all try—as women especially—we try on different identities.” By the film’s conclusion, Tai has found the perfect balance in her personality—and, of course, it’s reflected in her clothes: “The end is really beautiful when we see her at the skatepark. She’s herself. She’s got this cute little skate look—the striped t-shirt, a little headband, and the braids. She learned something and now she’s truly herself. It was really beautiful.”

Practically, the challenges of putting together the costumes for a film like Clueless were immense. It was, after all, the “analog” times. “I really had to find the pieces. I had to buy a big book called Collezione to see old fashions from the runways—to see what was happening in London, in Paris,” she recalls. “It wasn’t really that easy. And I had a very conservative budget—63 changes for Alicia Silverstone, 40 changes for Dionne, and Tai. And everybody else!”

“Everybody else” was hundreds of extras—all of whom arrived in their own grunge clothing each morning and needed a brand-new Mona May-approved look. “We had to change them head-to-toe,” she says. “Every extra that you see on the screen—we gave them the clothes, we gave them the shoes, we gave them the backpacks, we gave them the hats, you know.” As for sourcing the clothes, May went everywhere from the thrift stores to the mall.

It was, in other words, a painstaking, exacting process. Ultimately, May was thrilled that her costumes had the chance to shine on the screen thanks to the film’s Director of Photography, Bill Pope. “It wasn’t like normal films where you just see a wide shot and then a close-up of the actor’s face,” she explains. “He really took the camera, and the camera gave us the eye of fashion.”

Clueless wasn’t expected to take off the way it did. Upon its release in 1995, it garnered $10.6 million on its opening weekend and quickly became the number one movie in America. Its impact on teen fashion was instant, May recalls. “I mean, it was crazy. On the streets, you would suddenly see the girls wearing the coolest stuff.”

Did May single-handedly end the grunge era? Well, she certainly contributed to a new explosion of color and experimentation. The film was a reminder that fashion should and can be fun, and May thinks that young women at the time were ready for it. “It really was a very special moment for that movie to come out,” she says, “where I feel like girls were ready to step up and change the threads from the baggy to the feminine. And it was an international kind of craziness.” 

Of course, many films are released and have a temporary impact on culture. Barbiecore and Challengers are just a few recent examples. But few films are able to make their impact felt for decades to come. Clueless continues to be transformative to this day. Young women still watch it and still find themselves taking inspiration from Cher and Dionne, trying out a plaid skirt suit moment or donning a red slipdress for a house party. 

“It’s amazing. I don’t even have words. It’s so beautiful that a film can have such an effect on generations of women,” May says with emotion. “I meet women, and they all have stories about when they saw Clueless first. And how they started sourcing their own clothes, or they went for Halloween as Cher and Dionne. It’s a great testament to how [we] created something that touches people’s hearts.”

Mona May’s book, The Fashion of Clueless will be released on October 5, 2025.