The Stories Behind Clueless’ Iconic Costumes: From a Red Alaïa to Legendary Yellow Plaid

25 years ago, a movie came along that changed yellow plaid forever. Its name is Clueless. 

While it’s hard to believe a quarter-century has gone by since director and screenwriter Amy Heckerling introduced Cher Horowitz and her stylish California high school posse to the masses, the passage of time has hardly been noticeable given Cher and co.’s enduring influence—particularly when it comes to the clothes.

On YouTube and TikTok, budding fashionistas who were not yet born when the film debuted offer tutorials in recreating the characters’ iconic looks. In 2014, Iggy Azalea‘s music video for “Fancy” imitated the coming-of-age hit. And, come October 31, you’d be hard-pressed not to come upon at least one pair of BFFs impersonating Cher and Dionne in their Halloween renditions. 

Of course, such a legacy would not be possible without the film that started it all and the team behind it, helmed in part by costume designer Mona May, whose career credits include Romy and Michele’s High School Reunion, Never Been Kissed, Enchanted, and most recently, Santa Clarita Diet. But, before it all came Clueless. 

“It’s such an amazing experience to have to be able to kind of change what girls were wearing at the time and now lasting that long. 25 years later, it’s so crazy that it’s still so fresh in a way,” May exclusively told E! News. 

The story, according to May, begins with a pilot that both she and Heckerling had worked on. While the show was not ultimately picked up, the two hit it off creatively and Heckerling tapped May to not only costume design, but to infuse the film with more of a European fashion sense considering May’s own international upbringing. 

But, as May recalled, researching what was happening in fashion beyond the borders of America’s grunge trend at the time was not as simple a task as it is in the digital world of today. “All my research had to really happen kind of the old-fashioned way. I had to get the magazines from the runways. They were $80,” she described. “I had to really figure out what’s going on in London and Milan, what’s in Paris.”

At the same time, she and Heckerling kept the looks age-appropriate while embracing femininity. The result? A group of really well-dressed teenage characters. “I think it was like a really cool blend of the high fashion and then seeing it from the point of view of a high school girl,” May said. 

Because of the film’s smaller budget, May veered away from dressing the cast in designer looks from head to toe—a trend of the time—and instead created a mix of high and low fashion, resulting in very original, but still wearable ensembles that would continue to make an impression on generations to come.

Looking back on those one-of-a-kind costumes, May confirmed she has no regrets. “I think that what I was able to do in the time and money and kind of the innovation and how I pulled it off, it’s phenomenal,” she told E! News.

“I have to truly pat myself on the back because it was not an easy movie to do, to really find the ideas, translate the ideas, make it so cool…It’s just sheer kind of genius and hard work and dedication and love that made it happen.”

In honor of the movie’s 25th anniversary today, revisit some of those beloved looks and the stories behind them in E!’s gallery below:

“She had to shine. She had to jump out of the page, of the screen,” costumer Mona May told E! News of what they wanted for Cher Horowitz’s opening scene look. “We tried red and we tried blue, which is kind of like a more of a blond color, and nothing really had the pop, and when I found the yellow suit, the Dolce & Gabbana, and we put it on in the fitting, it was like sunshine, like a ray of sun just entered the room and that was what Amy [Heckerling] loved and everybody in the room reacted to it so incredibly because it really—you wouldn’t think of yellow for a blond girl…But, that really was the perfect thing to embody her in that first scene.”

As for the choice of plaid, “It had to be plaid. It’s just quintessential school,” May said. “You’re taking this very much of a Catholic school uniform and now twisting it to high fashion and then transforming it yet again through the eyes of the high school girl.”

While the yellow plaid has since become synonymous with the film, the Clueless wardrobe also featured another standout take on the pattern in the form of Dionne’s black, white and red version. As May explained, she made the outfit to go with Cher’s look so that they both were in plaid without clashing. May added vinyl lapels to the suit, which ended up coordinating perfectly with the KOKIN hat she found to complete the look. “When I saw that hat, it was absolutely the most perfect thing to go with the suit…the vinyl texture of it, the flower that matched the outfit. It took it to the high fashion.”

From Dionne’s opening black, white and red flower KOKIN hat to the various headgear that followed in the course of the movie, it was clear May had a thing for hats. “I wear hats all the time. It’s kind of my signature,” she told E! News. “When I brought hats to the table, Amy was delighted and I just was squealing because I love hats. I think they’re just such a great fashion accessory and it just really puts the outfit onto another level.”
 
May explained that the brand KOKIN made many of the hats for the film and she also sourced hats from thrift stores and costume houses. “That Dr. Seuss hat with the little swirl—who knows where it came from…probably a thrift store,” she said. 

While fashion was basically a bonus character of the film, getting designer clothes was no easy feat. “That was pre-PR,” May recalled. “There was no one sending us clothes.” Given the movie’s smaller budget, May relied on buying off the rack and spending money on what she made sure they definitely wanted. The famed red Alaïa dress, now a staple garment of the film, required further hoop-jumping. “We had to like find somebody who knows how to get to him [Azzedine Alaïa] and borrow the dress, but then we had to make sure that we can alter the dress to fit Alicia [Silverstone] and it was going to be on the ground, so if it ever snags, can we return it?” May remembered with a laugh. 

For Cher’s frenemy, Amber, their relationship inspired her over-the-top looks. “I think Amber always wanted to kind of be [Cher] and then took it to the tenth degree,” May said. “She was a little bit of a fashion victim and that’s where we kind of always looked at her clothes.”
 
“It was so much fun,” she added. “We basically all were coming to work and going, ‘Ok, what crazy look can we do for Amber?'”

For Cher’s retro love interest, Christian [played by Justin Walker], May channeled a few other Hollywood stars. “I always felt when I saw him that he kind of had something with like James Dean to me…a little bit of an old, old movie star look,” she told E! News. As a result, his wardrobe featured jackets and pleated pants reminiscent of ’40s style, paired with tight T-shirts for a Marlon Brando-esque look.