In our honest opinion, Clueless is one of the most iconic, most heavily recited and referenced, most eternally chic film in history. That means, Cher Horowitz, played by Alicia Silverstone in the 1995 cult classic, with her loqued-out style is (and will continue to be) forever immortalized as a fashion icon (it's currently streaming on Netflix, FYI). The matching yellow plaid set that her closet picked out for her? The red party dress ("You don't understand, this is an Alaïa!")? That little white Calvin Klein slip? Her most capable driving outfit? It's all so, so good.
But at the time of filming, the one person who didn't think anything of the fashion was Silverstone herself. "I remember I was really annoyed by it all," Silverstone confesses when we quizzed her about the clothes. "I was so young, I had only been working as an actress for two or three years at that point, and I didn't understand why there were so many fittings. I was like, 'Why are these clothes so important?!' I was annoyed by [costume designer] Mona May, who I thought was mean because she was always yelling at me about the clothes."
Silverstone says she had to endure something like 67 outfit changes, which meant countless fittings. But it wasn't until the film was released did she understand the importance of fashion in film.
"I can say all of that [about Mona May] now because we're very good friends and I think she's brilliant and I love her," Silverstone says. "The clothes played such a major role, and I was so impressed and I said to her, 'You're so good; sorry I secretly hated you the entire time." Silverstone laughs and then takes it back. "Not really, but you know, I resented all the attention on clothes, because it was exhausting having to go to all those stupid fittings!"
Back then, at 18-years-old, fashion just wasn't a priority for the star. She says she was a tomboy, the "complete opposite of a fashion icon," with an off-duty uniform that comprised T-shirts, sweats, and sneakers. "I just didn't pay attention to all that stuff," she simply says. "I just didn't get it." That's changed, though. Now, she's really into dressing up.
"It's only lately that I've been like, 'Oh, I want to be a woman,'" Silverstone laughs. And when asked about which of Cher's clothes she'd wear today, she calls out that famous Alaïa dress. "But I love all the costumes; they all looked great, and I think it's amazing when people look to Cher or dress up as her—that's the brilliance of Mona May and [director] Amy Heckerling."