"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.