The Style Strategy Behind Clueless’ 3 Iconic Characters — & Why The Looks Remain Relevant Today

I was in 5th grade when Clueless and its iconic fashion entered my life. As a spunky pre-teen with a burgeoning love for clothes, this film resulted in an awakening of sorts for my closet. Almost overnight I found myself trading my overalls and skorts (remember those?) for vinyl pants, plaid mini skirts, baby tees, and chunky Mary Janes. Cher Horowitz, Dionne Davenport, and Tai Frasier became my fashion idols, helping me navigate the daunting world of junior high with a little more confidence and, dare I say, style.

Fast-forward 25 years later (whoa) and I admit that the film that shaped my “look” as an awkward tween continues to leave its mark on me as a grown woman of 34. Candy-colored suiting, whimsy hair accessories, and knee-high hosiery can all be found in my closet today. So, you can imagine my delight when I managed to land an interview with the woman responsible for the looks that molded my fashion sense, Clueless costume designer, Mona May.

As it happens, my waxing poetic over the ‘90s teen rom-com’s imprint on my childhood is not anything the veteran stylist hasn’t heard before. In fact, May gets gushing monologues about her work on the film on an almost daily basis. “It warms my heart to hear that [praise] from so many women, and how emotional people are about this movie,” says May during our phone call. “It’s shaped them and how they view things. It’s incredible. As a costume designer you don’t set out to do that.”

However, when she was approached by director Amy Heckerling to oversee costume design for the 1995 film about young Beverly Hills teen Cher (played by Alicia Silverstone) and her fashionable best friends Dionne (played by Stacey Dash) and Tai (played by Brittany Murphy) as they experience heartbreak, triumphs, and the occasional makeover montage, May knew she wanted to venture beyond the grunge landscape that covered the fashion industry at the time. “When (Amy and I) scouted high schools, everyone was in big jeans and giant t-shirts — it was pretty much Kurt Cobain and Nirvana everywhere,” recalls May. “So, it was about creating a completely new world.”

New world indeed. With research and inspiration drawn from European runways, some of the most memorable fashion movie moments were born: Cher and Dionne’s coordinating plaid skirt suits, Cher’s barely there Calvin Klein dress, Dionne’s bold top hats, and, of course, the infamous Alaia (who's, like, a totally important designer) that the blonde protagonist got robbed in.

Although some of the ensembles were custom creations of May's, many were sourced from places the film's three characters would probably shop from. "We had plaid designer suits, but then vinyl skirts from funky shops on Melrose," says May. "I was also shopping at Fred Segal, because they were fresh and bringing stuff from Europe that was very up-to-date and fashion-forward."

While I've always felt a kinship with all three of Clueless' leading ladies, May had a close, personal relationship with them. She had to. To fully grasp their wardrobe, she had to get into the characters' mindset and understand how they each viewed the world and what their journey through the film would entail. "I love diving into the psychological [perspective of the characters]," says May.

Ahead, May breaks down her approach and vision for Clueless' three female stars, who managed to make fashion history in two hours of movie magic.

Clueless’ Iconic Fashion Decoded: Cher Horowitz

"Amy and I spent a lot of time talking about who Cher is," recalls May. "She was very couture and sophisticated in her way of dressing, even though it was youthful. It was very perfectly tailored and there was a specific color palette she liked. She loved the empire waist, little cap sleeves, and there were always the twin sets."

The costume designer compares the young blonde protagonist to Grace Kelley, in that there's a "timelessness" to her look. "The peacoat she wears, the beret, the little leather jacket with the A-line leather skirt," says May. "When I look at her clothes, I don't think they will ever go out of style. She's very Euro-fashion, French girl."

Clueless’ Iconic Fashion Decoded: Dionne Davenport

For Cher's no-nonsense best friend, May said she was able to push the fashion boundaries a bit more. "She was more risqué, so we did shorter skirts, but just enough that was still acceptable for a high school girl," explains May. "She had the leopard, the neon, the vinyl, and the '50s purses. She was much more adventurous, so we had a brighter, super-fun color palette for her."

And, as for the story behind the game-changing top hats Dionne became known for (particularly the black and white one worn in the film's opening scene): "I met this designer named Kokin through a friend," recalls May. "He's a milliner from New York City, and I loved his hats, because I myself wear a lot of hats. When the movie was prepping, I reached out to him, and the hat was created. [...] To me, as a fashion person, hats add so much to an outfit."

Dionne's signature accessory became all the rage in the '90s, with teens wearing all manner of sky-high top hats in various color-ways, materials, and patterns. To this day, hat designer Kokin includes embellished top hats in his collections ... Dionne would definitely approve.

Clueless’ Iconic Fashion Decoded: Tai Frasier

For Cher's grunge-turned-couture friend Tai, May said she had more room to go for "the arch" in her storyline. Starting off in baggy, oversized clothing, with little to no knowledge of trends or designers of the moment, Tai became the ideal target for a classic movie makeover.

"She becomes a mini-me of Cher, wearing plaid co-ordinated outfits, maybe not coming from high-end designers, but coming from the mall," says May. "She probably shopped at Contempo Casuals and tried to be Cher. But then she kind of evolved into who she is [at the end of the film], becoming this young, youthful sporty girl with striped t-shirts, her little pigtails, cute headbands, and sparkly necklaces. If you look at the bookend versions of her at the beginning and end of the film, it's the same person, but — now — improved. When she was dressing like Cher, she really wasn't herself."