This July marks the 20th anniversary of Clueless, Amy Heckerling’stouchstone teen comedy that introduced the kids of America to a totally new lexicon, and inspired many to retire their grunge apparel in favor of finding their inner Cher Horowitz. Even two decades after the film’s premiere, the clothing worn by star Alicia Silverstone is still so timely that it influences runway designers and new generations just discovering the 90s classic. In celebration ofClueless’s emblematic styles, we spoke to both Heckerling and costume designer Mona Mayabout their collaboration, the unlikely ideas behind Cher’s wardrobe choices, and the genesis for Cher’s virtual closet.

When Heckerling was writing the Clueless script, she knew that the characters’ clothing would be integral because it “would be one of the areas of comedy—that the characters would rag on each other’s clothing,” she told us by phone. Growing up in New York City, she herself was not particularly a fashionista, but she went to school with a few. “I went to art and design high school with a lot of people taking fashion. They would get up in the morning and what they put on meant a lot to them. There was a very creative element to what a young person feels like they can do and wear. I wanted to have fun with it and make it look pretty.”

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Heckerling and May visited Los Angeles schools in the mid-1990s to get a sense of what high-school students were actually wearing—flannel and loose-fitting jeans, none of which fit Heckerling’s ideal aesthetic. “It was just dreadful,” May said of grunge fashion. “The plaid shirts and baggy pants, and girls looked so masculine. There was really none of the girliness.” Knowing that Clueless’s central shopaholic would not be caught dead in flannel, Heckerling and May took wardrobe liberties, creating whimsical costumes that were both smart, feminine, and flattering. “I wanted that feel of a fantasy that you would like to live in,” Heckerling explained.

Since there was no Internet or Net-a-Porter, May reasoned that Cher and Dionne would look to runway styles to inform their closets, especially since they had the money to fly overseas to European fashion shows. In addition to drawing on designer wear, the two also incorporated their own style preferences into Cher’s and Dionne’s costumes.

“The one thing that I totally loved and wanted, which was out of style when we did the movie, was over-the-knee socks,” Heckerling said. “Over-the-knee socks remind me of the 1920s, silent films, and the stars of the era who wore the rolled-down stockings. They sort of referenced that in Cabaret, when Liza Minnelli was singing ‘Mein Herr,’ and I love the way she looks in that scene.” There could be another reason why Heckerling is partial to the look: “I guess it’s because I hate every part of my body, but I have thin thighs,” she laughed. (If you are planning your Clueless Halloween costume, be careful to make an important hosiery distinction: Cher wears over-the-knee socks—not knee socks, which Heckerling says she hates.)

Another integral accessory were fashion-forward hats, many of which were worn by Dionne. “I always get hats, but never have the nerve to wear them,” Heckerling said. “Hats are a thing that are really stylish, but you have to have the confidence to pull it off. And Cher and Dionne do. At the time there was that rave culture, where for a brief moment in time people were being more creative with their clothing. And you would see a lot of crazy hats at raves—like a top hat or Dr. Seuss hat, and Mona found a way to make them stylish.”

In the past few years, there have been news stories about Cher’s incredible virtual closet now being a real-world possibility. But Heckerling says that she got the idea from a music-industry producer, who had the futuristic fashion gadget in his home decades ago. “A producer in Hollywood had very wonderful clothes, but he felt like you always pull the same thing out of your closet because you don’t really see everything. So he thought, Why not have a device like they have in dry cleaners, which rotates your clothes? So he got somebody to make it for him. I saw it and I thought, Oh my God, someday I am going to use this in something.”

Ahead, Heckerling and May discuss several specific Clueless costumes.

“At first Mona had other outfits for Cher and Dionne for the first day of school,” Heckerling said, “but she was worried that Dionne’s outfit would completely overwhelm Cher’s outfit. She said she was losing sleep. It was driving her crazy. So when she came up with the yellow suit, it was like, ‘Nobody is going to top her in that.’”

“Dolce & Gabbana did the yellow suit,” May said. “And then I made the Dionne suit. For the movie, I mixed thrift store with designer because I did not have a lot of money in my budget to buy designer things. It was about taking fashion from all different sources and predict what would be on the street six months ahead, like a fashion designer would. Amy and I both love plaid, and I think there is nothing better to have than a quintessential plaid skirt for a girl’s first day of school. But we had to go further with that [idea] for the movie, so we had to have the complete suit.”

May also pointed out that “Dionne’s skirts were always a little shorter because she was the sassy one and she wasn’t a virgin.”

In Clueless, Cher and Dionne call each other every morning to coordinate their outfits, ensuring that they will always complement each others’ clothing. Heckerling told us that if she had more money in her budget, however, she would have coordinated every characters’ costumes like she did with the girls’ gym clothes.

“There was kind of an ongoing seasonal color palette, so in the fall, Cher and Dionne are wearing reds, yellows, and oranges. In the Christmas scene, where they are at the Valley party, everyone is wearing red and greens. And then in the end, when Christian arrives, it’s the beginning of spring, so that’s when the pastels and the pink fluffy pen come in.”

“There were some costumes you would see throughout all of the seasons, like the girls’ gym outfits. I figured they had to be black and white so they would go with [each different seasonal palette].”

“We imagined that there was a wardrobe code for what the girls could wear in gym, which was black and white clothing,” May added. “And if that was the case, we could make their costumes different and flattering for each actress, while sticking with the black-and-white theme.”

“Everybody has a very specific look to their character,” May explained of differentiating costumes. “If you look at Amber and her crazy stripe outfit . . . Amber always dressed in theme, she had the sailor look or the Pippi Longstocking look (seen below).”

For Dionne’s costume here, May added white cuffs and a collar to a cranberry-colored velvet dress. “To me it is so French, so classic and chic. I love Jean Seberg, Brigitte Bardot, and all of those French girls of the time that were so feminine. It is all about the beauty of a woman’s body and femininity. And I gave her a matching headband and the socks.”

For Cher, May explained, “This is actually a quite funky outfit for Cher because it is a suede vintage skirt that she is wearing with silver snaps in the front. It is almost a little bit 70s, with the little sweater vest and the oxford shirt. You could almost go to Brooks Brothers now to buy this.” May adds that the over-the-knee socks not only accentuate Silverstone’s legs—one of her best assets, May discovered during fittings for Cher’s 60 costume changes—but they “pull the looks together.” And, strangely enough, when she talks to men about the movies, those socks “are what they remember.”

Brittany Murphy’s character, Tai, has a more middle-class background than Cher and Dionne, so May was careful when creating Tai’s costumes to make a class and style distinction. “She really represented the moment, of what it was like in high school at that time,” May said. “Even after [Cher] did her makeover, we were careful not to make her as sophisticated as Cher would be.”

When Heckerling was writing the script, she was not sure which dress she and May would be able to get for Cher’s Valley party and robbery scenes, so she tinkered with dialogue once May secured a cherry-red Alaïa cocktail dress.

In the latter scene, Cher is left stranded in the Valley. An armed robber appears, and orders her to lay on the ground face- down.

“You don’t understand,” she counters. “This is an Alaïa.”

“An a-what-a?”

“It’s like a totally important designer,” she explains.

Cher is also wearing Jimmy Choo shoes. If you look closely in the film, you will notice that neither Cher nor Dionne wear stilettos (or low-cut tops) for a good reason. “I wanted the movie to have a fresh innocence,” Heckerling said. “Not, ‘Hi, I’m 15 and I’m in five-inch heels and here are my breasts.’ I find that repulsive.”

“All of the shoes were really important for me and Amy,” May said. “That is why there are no stilettos. We had a lot of Mary Janes, cute little sandals. It’s part of being a girl in high school, not a slutty model walking on the runway.”

To round out Cher’s accessories, May created a Chanel water-bottle holder, which Karl Lagerfeld put on his runway after Clueless premiered.

“[Cher’s power-shopping ensemble] is partly this one outfit I really loved that I designed for when Cher is depressed,” May said. “She is walking around Beverly Hills really sad. She is wearing a white chiffon blouse, almost like a tuxedo shirt with ruffles in the front and the little silver short vest and the argyle skirt. And we threw the little blazer over it. I don’t think the outfit was in the movie as much as promos. It was a little more grown-up. Very chic, very big city, very European.”

Viewers will notice that Cher does not wear jeans, and for good reason says May. “There were not that many sophisticated jeans then—the dark jeans and Rag and Bone. We kind of reserved the jeans for Tai because we really wanted to show a different class—she came from more of a middle-class America. We wanted to show the difference, especially when we first meet her, in her grungy outfit du jour.”

May still sees people channeling her Clueless costumes. Alexander Wang, who has citedClueless as his favorite movie, put a sheer white blouse and leather skirt on his runway recently, according to May, that was very much inspired by one of Cher’s signature looks. The costume designer said that when young people discover she is responsible for Cher Horowitz’s clothes, they fan out, telling her how they emulated the character’s fashion. Even girls who weren’t born when Clueless premiered pay sartorial homage to the quintessential 90s film.

Two years ago, May attended a Hollywood Forever Cemetery screening of the movie, and was shocked to see the new kids of America dressed from head-to-toe in homemadeClueless clothes. “They made Dionne hats and were wearing patent leather skirts, fake fur, and over-the-knee stockings. Some were even dressed as Miss Geist with the smeared lipstick, crazy hair, and glasses! How often does this happen in your career when you have this kind of impact on so many girls?”

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