‘Clueless’ Costume Designer Mona May On The Film’s Enduring Relevance, The Genesis Of Her Book & Why AI “Doesn’t Have My Level Of Taste

The enduring legacy of the 1995 film Clueless is currently experiencing a major renaissance, led by its legendary costume designer, Mona May. To celebrate the film’s 30th anniversary, May has released her new book, The Fashion of Clueless. This richly illustrated volume offers a deep dive into the creation of Cher Horowitz’s instantly recognizable wardrobe, from the iconic yellow plaid Jean Paul Gaultier suit to Dionne’s signature hats. 

The book features never-before-seen sketches, behind-the-scenes photos, and fresh insights from May, as well as interviews with star Alicia Silverstone and writer-director Amy Heckerling, confirming the film’s status as one of Hollywood’s most influential fashion texts. Even the cover feels expensive, and you can tell it was designed by someone with a keen eye for fashion, like a costume designer. As May points out, the choice of fabric, the detailed stitching, the tag, and the raised graphics were vital to making it chic, a deliberate choice to mirror the film.

For May, the process of creating the new book was more than a publishing venture; it was a personal chance to reconnect and reminisce with a cast she hadn’t spoken to in years. While she remains close with Heckerling and Silvisertson, the project allowed her to catch up with the rest of the group, feeling as if no time had passed. The conversations brought back forgotten memories and surprising production details, like Paul Rudd reminding her that, in the early days, he famously wore his own jeans and shoes on set.

The shared experience of making the movie was formative for the young ensemble, a true launchpad for everyone involved. She recalls the powerful, career-making impact of that time. “We were so young when we made the movie, I mean, truly, it was, like, my first big feature, a studio movie, and Paul Rudd’s first feature. Alicia was a little bit more experienced. Stacy Dash had done some stuff. But, you know, Breckin Meyer, all those guys, and Donald Faison, we were like, babies. So it’s such a bonding time. And then when the movie came out, it put us on the map, all of us. Every Hollywood door basically opened.”

Beyond the friendships, the book creation also served as a reminder of the foundational, transformative creative partnership she shared with director Amy Heckerling. She credits the director with fostering her talent and giving her the necessary artistic freedom to truly develop her craft. “Amy truly took the genie out of the bottle and allowed me to be this creative person; she allowed me to truly become the artist, and opened up to all my talents.“

As the film hits its 30th anniversary, its enduring and evolving cultural relevance continues to resonate with a new generation of fans, even in an evolved digital age. For those who created its world, this sustained success lies in a blend of emotional nostalgia and timeless design. The primary explanation is the depth of connection fans continue to feel, often across generations. “It’s amazing to me that the movie has this sustaining power. I see it at book signings and art schools as moms come with their teenage daughters, and they all feel this emotional connection. Beyond the fashion and actors, I think there is a nostalgia for a kind of innocence we’ve lost—the femininity, the girliness, the friendship—all of it is trapped so beautifully in this film,” explains May.

“Because I’m European and traveled extensively, I had a very global point of view when designing. I wasn’t just designing for LA; I wanted something super chic and timeless, like the films of Sophia Loren and ‘Breakfast at Tiffany’s’. The movie still gives the audience something to relate to because the fashion is so contemporary and wearable. That’s what draws the kids in—it’s a big deal and honor that they still think it’s cool, because they are very sophisticated these days.”

Pre-1990s cinema offered few examples of iconic, visually defined female fashion pairings, making Cher and Dionne’s coordinated style feel groundbreaking. Despite the existence of numerous famous past duos like Thelma and Louise, or Marilyn Monroe and Jane Russell in Gentlemen Prefer Blondes, none were defined so much by the meticulous, coordinated presentation of their clothing.

May recalls, “When Amy wrote the script, no one in Hollywood wanted to make this movie. She went from studio to studio, and they’d say, ‘It’s a movie about girls. You can put some boys in it, and we’ll make it.’ It wasn’t until Paramount—and specifically Sherry Lansing, who ran the studio at the time, and Scott Rudin—that they finally said, ‘Okay, we’ll do it.’”

Far from being ‘totally buggin’,’ the cultural relevance of Clueless remains undeniably strong three decades on. The film’s iconography was recently officially solidified at Anna Wintour’s Vogue World 2025 at Paramount Studios in Los Angeles. Celebrating the link between cinema and style, the event featured the movie’s unforgettable duo in plaid suits on the catwalk, alongside other characters from Hollywood history, a powerful tribute to the lasting influence of May’s vision. 

The experience of celebrating the film’s legacy provided May with a significant full-circle moment. “The movie was made by Paramount, shot on the Paramount lot, and 30 years later, I am here on the lot, seeing the girls on the runway, right in between the stages where we made the movie. It’s unbelievable, and an emotional moment.”

For the show, the costumes were designed in collaboration with Vivian Westwood, recreating Cher’s tweed look, and Tom Brown designed Dionne’s outfit, as the original costumes are gone. May explains, “I think at some point, Alicia had the costumes. She was young, and she didn’t know what to do with them. We don’t know where the costumes are. And, you know, 30 years later, things do disintegrate. We were able, thank God, to still have the hats, which was great.”

Looking ahead, the question on many designers’ minds is: What do you believe is the single biggest, inevitable change coming to the craft of costume design? Is it driven by digital costuming for virtual reality, greater demand for sustainability, or something else entirely? For May, the most interesting and rapidly advancing factor is Artificial Intelligence, but she remains confident that the human element of taste and emotional nuance will preserve the artist’s role.

“I think the AI is very interesting as it’s moving so fast. I feel that, as a costume designer, my role is going to still be very important, because I don’t think that AI will have the level of taste that I have. I don’t think you can teach it unless they plant something in my brain and steal it! I don’t know if AI can really do a fitting, the real clothes. If we are still using real clothes, my role is there.”

May argues that even in a digital future, human expertise remains crucial for authenticity and quality.  “And I think even if it’s digital, my role is there because I know proportion. I know what fits an actor. I know the emotionality of something. I know that it has to be dirty or too tight or too loose—I don’t know if that is AI’s strength, definitely not yet, because those are the things I think, as a writer, too… I don’t know if certain things are so emotional that they are so important to make the characters authentic, that are available to that brain of AI.”

She concludes that true artistry will always require a human touch. “I think they still will need me if the quality is what they want. I think there’s going to be a lot of stuff that’s just going to be very low quality, fast, and cheap. I think truly, when you want this to be art, and on a certain level of artistry, we will still be very important and playing the part. I mean, AI is great when you’re doing a presentation, and you can do a different color, and show the dress in 10 colors and shorter and longer. All of that is great. That’s just a shorthand.”

In a climate oversaturated with digital information, the question of how May stays current in trends is critical to her craft. The designer employs a relentless, immersive approach, constantly seeking inspiration from the physical world. “I mean, you know, all the magazines, Instagrammers, friends, events, travel,” she explains. “I go to Berlin, where my mom lives, a lot. I go to London, I’m here in LA constantly, in New York, seeing what’s happening on the street. I love street fashion, and just that inspires me. I totally take pictures of people secretly.”

May describes herself as a “crazy, maniac, creative person” who needs to be constantly fed with visuals to maintain her artistic “pool.” But simply consuming information isn’t enough; the crucial step is filtering it through her unique lens. “I just need to be filled so I have a pool of art and images in the back of my head to pull from.”

“And, you know, again, Clueless is my baby. It’s my point of view on fashion—it’s the way that I see the world. Lucky that that really was a winner, that made an impact.”

May has since created memorable looks for other beloved films, including Romy and Michele’s High School Reunion, Never Been Kissed, Enchanted, and The Wedding Singer.  The book is a dazzling tribute to one of the most influential style films of all time and is being hailed as the ultimate guide for readers to channel their own “main character energy.” 

Mona May’s The Fashion of Clueless (Insight Editions; hardcover; $28.99) can be purchased here.