"Do you prefer 'fashion victim' or 'ensembly challenged'?"

Can you believe it's been 20 years since Cher Horowitz said that? With timeless one-liners and the most enviable wardrobe of the 90s, it's no surprise that we're still obsessed with the hit film Clueless.

In fact, two years ago costume designer Mona May attended a screening of the film and was shocked to see a new generation of American teenagers dressing as Cher, best friend Dionne Davenport, Amber Mariens and other characters in over-the-knee stockings, homemade hats, fake fur and patent leather skirts. “How often does this happen in your career when you have this kind of impact on so many girls?”

In celebration of this, May and director Amy Heckerling finally came together recently to open up about what inspired the film's signature looks. 

Speaking to Vanity Fair, Heckerling said she that while she was writing the script, she knew that the characters’ clothing would be integral part of the dialogue: “(It) would be one of the areas of comedy—that the characters would rag on each other’s clothing”.

She also knew the fashion had to be feminine, whimsical and fun. Heckerling and May visited schools in Los Angeles in the mid-1990s to get a sense of what high-school students were wearing at the time, only to find flannel, loose-fitting jeans and grunge fashion - none of which fit the pair's aesthetic vision.

“It was just dreadful,” May said. “The plaid shirts and baggy pants, and girls looked so masculine. There was really none of the girliness.” They took matters into their own hands and conjured up a truly unique and memorable style for Cher and her friends. “I wanted that feel of a fantasy that you would like to live in.”

Take a look at the fascinating stories behind each style decision below.

First day of school outfit

“At first Mona had other outfits for Cher (played by Alicia Silverstone) and Dionne (Stacey Dash) 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 added: “Dionne’s skirts were always a little shorter because she was the sassy one and she wasn’t a virgin.”

Over the knee socks

“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.”

But there's a more personal reason why Heckerling was in favour of the look: “I guess it’s because I hate every part of my body, but I have thin thighs,” she laughed.

May added that during fittings for Cher’s 60 costume changes, she discovered Silverstone also had great legs. The over-the-knee look not only accentuated her figure but that it “pull(ed) the looks together.” The socks went onto become the most iconic style from the films.

Mary Jane shoes

Cher and Dionne never wear stilettos. “I wanted the movie to have a fresh innocence. Not, ‘Hi, I’m 15 and I’m in five-inch heels and here are my breasts.’ I find that repulsive,” Heckerling said.

“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.”

The white collars

May transformed Dionne’s cranberry velvet dress by adding white cuffs and a collar. “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.”

Speaking about Cher's ensemble here, May said, “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.” 

Brittany Murphy’s character, Tai, comes from a more middle-class background than Cher and Dionne, so May carefully crafted her outfits to make that 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.”

Cher's shopping costume

“(This) is partly this one outfit I really loved that I designed for when Cher is depressed,” said May. “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.”

The Alaia red dress

When Heckerling wrote the scene which sees Cher attend a Valley party and then be ordered to lay face-down on the ground when armed robbers suddenly appear - to which she replies “You don’t understand,” she counters. “This is an Alaïa.” - the director didn't know which dress May would be able to get for the scene.

She ended up tinkering with the dialogue once May secured this cherry-red Alaïa cocktail dress.

Why there was a no jeans policy for Cher

May said: “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.”

Dionne's outrageous hats

“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.”

Cher's virtual wardrobe

“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," said Heckerling. "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.”

Image: Rex Features, YouTube