Alicia Silverstone Was Pretty 'Clueless' About Fashion Before the Film

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Cher knew her way around Rodeo Drive. (Everett Collection)

Alicia Silverstone rocks every one of her 60 costume changes in ‘Clueless.’ Her preppy plaid miniskirts, sophisticated slinky dresses, and glam accessories are much of what makes the teen movie a classic.

As the fashionable film marks the 20th anniversary of its release on July 19, costume designer Mona May revealed to Yahoo that Silverstone wasn’t exactly a natural when it came to pulling off her character’s memorable wardrobe. The actress — who’s now known for living a green, vegan lifestyle — was just 18 at the time, known for her appearances in Aerosmith videos, not on red carpets.

“[Alicia] was really young, and I don’t think she was really experienced with high fashion. When we brought all this crazy stuff, it was a little bit new to her,” May said at a recent screening of the movie in L.A. “We almost had to educate her on how do you wear the clothes, how do you feel in the clothes? It’s a whole different thing of running around with your dogs in your sweatpants, as she always does to this day.”

Related: The ‘Clueless’ Cast That Almost Happened: Reese Witherspoon, Ben Affleck, & Dave Chappelle

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Stacey Dash and Silverstone turn heads in Clueless. (Paramount Pictures)

Related: 'Clueless’ or Not? Katy Perry Shows Off Schoolgirl Style

“She was Cher in the sense of the innocence,” May continued. “Cher was never contrived, and I think Alicia’s heart is open like that, so it was fun to play with the clothes and teach her to be the high-fashion maven.”

The fashions of the day were a lot different than the ones Cher’s computerized closet selected for her each morning. May recalled visiting L.A. high schools with ‘Clueless’ director Amy Heckerling to gather inspiration for the film wardrobe and coming back very disappointed.

“It was 1994. We went to Venice High and Hollywood High and everything was grunge,” May noted. “You know, people were in the baggy pants… You couldn’t even tell who was a girl, who was a boy.”

Mona May describes her most famous film. (Paramount Pictures)

Eventually, May and Heckerling found what they were looking for on the runways of Paris, Milan, and London. They also found vintage pieces from thrift shops and low-end fashions from the now defunct Contempo Casuals and other mall stores. Mixing and matching pieces from different price ranges is something everyone does now, but no so much in the era of flannel shirts, baby doll tees, and overalls (preferably with one shoulder strap undone).

While Silverstone was tentative about fashion, actress Stacey Dash, who played Cher’s glam best friend Dionne, was already into style. Then 27, Dash had been appearing on ‘The Cosby Show,’ ‘The Fresh Prince of Bel Air,’ and other shows for a decade.

“Dionne was most excited, because she was a little older, she knew about fashion. She got it,” May said. “She kind of understood her body a little bit more. She was a little bit more open to play… a little more risqué.”

Brittany Murphy, Silverstone and Dash are fashion perfection. (Everett Collection)

Dash — now a contributor to Fox News — was quick to ask for skirts to be cut shorter and to add a touch of patent leather, for instance.

Although the ensembles that cast members wore in the film were selected for them, May said everyone offered input on what they liked and disliked, mostly because of things that they did or didn’t want to emphasize about their bodies.

“The process is amazing, and it really happens in the fitting room when they try the stuff on,” May said. “That moment is when you know it’s right.”

Twenty years later, it still is.