Thirty years ago this month, costume designer Mona May did something extraordinary. She put together costumes for a film that would define trends for the whole of the ’90s and beyond. Working closely with visionary director Amy Heckerling on a little project titled Clueless, about young women navigating high school growing pains — a departure from the common teen narratives at the time, which often centered on teens getting murdered, vanishing in the first 20 minutes, or switching bodies with their mother (The Heathers, Picnic at Hanging Rock, Freaky Friday).

Through their unique apparel, the female characters expressed their personalities and navigated the world in style. Nearly 20 years before social media turned fashion into content, the costumes for the film, particularly Cher’s yellow plaid Jean Paul Gaultier skirt ensemble that opens the film, became iconic. Any woman over the age of 30 has that image burned into their brain, right alongside Audrey Hepburn’s little black dress from Breakfast at Tiffany’s and Judy Garland’s blue gingham jumper and ruby slippers from The Wizard of Oz.

Clueless did something audiences hadn’t seen in a long time — it gave us a glimpse into the inner lives of teenage girls in the ’90s but also elevated their status as sartorial powerhouses. What is even more remarkable is that May pulled this off on a costume budget of $200,000. (The film’s overall expenditure was $12 million.) In a time when dark, moody grunge was dominating, the intentional beauty of Clueless was a contrast to what audiences were used to at the time. “Amy [Heckerling] wanted to make sure that these girls were very feminine and beautiful,” May tells TZR over Zoom. “We wanted to make sure that this film was very feminine, very pretty. You know, it was a movie about girls, which was also not a movie that was made before.”

And it worked. Clueless was a colossal hit, making a reported $88 million in ticket sales in 1995. Often labeled as the perfect high school film, it perhaps resonated so strongly because it gave millennials something they had been craving at the time: smart, sassy teenagers assessing the world with witty observations, confidence, and incredible style. The film’s language, take on teenage culture, and, of course, ensembles became permanent fixtures in the pop culture lexicon.

This is exactly why the celebration of the film 30 years later feels so earned, and why so many companies and brands are still interested in partnering with May on Clueless-themed projects and capitalizing on the film’s enduring relevance. In fact, the costume designer, who has a book coming out later this year on the fashion of Clueless, has collaborated with the iconic L’Ermitage Beverly Hills to launch “The Clueless Suite” along with Paramount Pictures and Bloomingdale’s and featuring Fitted, the official virtual Clueless closet app. Through Sept. 1, hotel guests will get to experience what it is like to be Cher Horowitz, even if it is only for one night. We’re all totally combelling.

May’s Clueless Style Strategy

When May was building the world of Clueless, she didn’t look at her job as just making sure the character was in a trendy outfit; she was equipping the actors with imperative storytelling tools. “I don’t just arbitrarily say ‘Oh, now I’m going to put her in a yellow suit.’ It’s a process figuring out what the scene is and what the emotional situation is,” May told TZR. This translates to a whole lot of wardrobe fittings. And for a film where the main character (played brilliantly by Alicia Silverstone) wears 59 looks alone, that is a lot of character development work.

May recalls a then 18-year-old Silverstone, already an outspoken animal activist, coming to hourslong fitting sessions with her two dogs, ready to work. The creative says these meetings were imperative for character development and for the actors to figure out how to wear the clothes. “How do you stand? How do you see each other? How do you learn how to walk, how to move, how to be in those clothes, and truly become the character?” May explains.

And, remember, this film was created before Amazon, Instagram, and Pinterest mood boards ever existed, not to mention instant access to runway archives. May fondly calls the making of the costume department for Clueless as completely analog. Physical in-person sourcing and extensive research had to take place to understand what ’90s teens would be buying from the mall and boutiques like Fred Segal. “We were mixing all the clothes from different places to create this very fresh, new look that never existed,” she says. “At the same time, we were showing audiences how to wear clothes differently. The highs and lows were really big at the time. The thrift stores mixed with the high end [brands], with the jeans, and then everything being tailored.”

Clueless In The Modern Age

But how would May, who went on to create the costumes for Romy & Michelle’s High School Reunion, The Wedding Singer, and Enchanted, dress the characters today in an age of TikTok uniformity? Now, we are constantly exposed to style that is formulated, immediately shoppable, and easily duped. The legendary stylist noted that because the costumes were so authentically assembled, they brought the characters to life. “They had to feel real, and the audience needed to connect with them,” May says. “They became real girls. They weren’t just models walking around in their threads head to toe.”

If designing for Clueless in 2025, May believes she would have a lot more PR involvement but worries that it would hurt the overall vision. “If somebody is head to toe in Calvin Klein in every outfit, it would be an advertisement,” she says. “I would want to continue to bring something very unique to each one of them, and source it from the designers but also from thrift stores.”

Though it would be easier — and quicker — to source clothes in the present day, May thinks the accessibility would almost create more challenges. “I think [teenagers] were much more individual [in the ’90s],” she explains. “And it was fun to create something that didn’t exist, that really felt super fresh. It is very hard now, because the times are so different. Now, we are in the age of Instagram; we have TikTok. Everything is much more kind of oversexed in a way. Everybody’s a fashion critic. And how could I keep and create this kind of innocence and timeless beauty? It would be challenging.”

In order to make it feel unique, she said it helps to stay within the parameters of the costume, helping to define the character. She said Cher would be much more kind of put-together, tailored. Maybe she’s more consistently in Chanel and Dior. Dionne Davenport would be a fun, funkier mix of high school-friendly runway looks. May’s goal was and always is to ensure the audience understands the characters immediately from the costumes. “You knew who Dionne was, you knew who Ty was, you knew who Amber was,” she says. The increase in awareness of sizes and sexual fluidity in modern society would be a bonus and “really fun to explore.”

A 2025 version of Clueless through May’s eyes would be an amazing sight to see, but the original is so perfect, it isn’t worth touching. It’s a total Betty.