The Crazy Thing You Didn't Know About Cher's "Clueless" Costumes, According To The Designer

Creating Cher's Iconic "Clueless" Costumes

Unfortunately, Cher's high-tech computer we see in the movie didn't actually exist at the time (" I don't think to this day anybody really has created anything better"), which means the research process for Cher and Dionne's Clueless costumes relied exclusively on books, school visits, and fashion shows. "Amy heckling really wanted to make sure that they're authentic characters," May says. "When you're a good costume designer and you're successful, I think you're really bringing these characters where the audience can find themselves in the characters...When you see an actor onscreen, they don't even have to say the line and by what they're wearing, you know exactly where they are in their lives."

When Clueless opens, Cher is in the middle of the very memorable time in any woman's life: high school. Because of her fashion-loving personality, and the fact the movie was avoiding the neutral, grungy aesthetic popular with teens at the time, May's team created more than 60 different costume changes for lead actress Alicia Silverstone.

"This is unheard of in the movies. So imagine all the clothes we had to get to create 60 changes, plus Dionne probably at 50, plus Ty, plus Amber and everybody else," May says. "We had to create the whole world of Clueless from the smallest thing of props to every extra that you even saw in the far background."

Color ended up being one of the most important — and memorable — aspects of the whole film. "The yellow plaid outfit...wasn't arbitrary," she says. "We tried red, we tried blue. It wasn't until she put the yellow on her, we were like, 'Stun, this is it. She's the sunshine. She's the ray in that moment.' So I think if we can bring that and be the ray as we walk out in the morning to our jobs or go on a date and feel amazing."

Everything about Clueless set it apart in pop culture, from the movement of the camera, to the costumes, to the way Silverstone embodied Cher.

"She was 18 and she was always an advocate for animals and running around in her sweatpants with two or three dogs [and she had to learn how] to become Cher from her own self," May says. "You see the detail, which I think also was such an exuberant journey of textures and fun and details that people really remember. So it was an incredible experience of these super creative collaborators and including actors and the director and something really unforgettable. I think that now lives on the screen to delight people 30 years later. It's amazing."

Turning Fantasy Into Reality With Amy Adams

Another film with a bubbly leading lady that's a delight to watch? 2007's Enchanted, which takes original character Giselle (Amy Adams) out of a cartoon fantasy kingdom and brings her to the scariest place of all: the real world. The movie is full of special appearances and Easter eggs, and the costumes highlight Giselle's journey from a Disney character to a real human woman.

"It was such a beautiful script. And it was iconic characters that I could give a little fresh kind of makeover, which I love makeovers," May says. "You really see the progression from the big poofy white dress to then the dress she makes from the curtain. It's still very princessy and she runs around in the park. Then she is in the little yet more contemporary dress, the one that I designed with the little flowers...I mean, it's still a little poofy on the bottom, but she could have bought it at Bergdorfs. Right?"

The journey in Enchanted culminates in a final ball, where Giselle shows up with a new dress unlike anything she's worn before, as well as a trendy haircut and smokey makeup. "The moment when she arrives at the ball and she decides, 'I'm going to stay here. I am human. I want to be human,' everything is stripped," May says. "I mean, the dress was completely body fitted. The color was very specific too. It wasn't black, it wasn't red, it was kind of a royal purple. The hair is slick. The skin is more imperfect now."

All of those details highlight May's favorite part of being a costume designer: embracing who we are. "I think really being able to tell these stories and empower girls [to] see themselves and being able [to ask] 'Who am I? And how can I love myself more?' To me, it's all about that," she continues. "It's really about loving yourself and loving your imperfections too."