‘Clueless’ Director Amy Heckerling and Costumer Mona May Break Down the Film’s Iconic Outfits

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After a quarter of a century, costume designer Mona May’s work on director Amy Heckerling’s 1995 classic teen movie, “Clueless,” remains iconic.

“Everybody was into grunge fashion when we made this,” she recalls. “We were having to look to the future and bring it to the table. We were inventing pretty much everything.”

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As Clueless celebrates the 25th anniversary of its landing in theaters on July 19, May and Heckerling look back on five key pieces of costuming.

Cher and Dionne’s First Day of School

May: As this was the first outfit, we needed to get it right. She’d be in the Quad, which was outside, there was going to be a lot of green. We tried blue, we tried red, but they didn’t have the right energy.

Heckerling: We originally had something else for Cher to wear, but Mona kept telling me she couldn’t sleep at night. She was worried Dionne’s outfit would shine, and Cher’s would disappear into the background.

May: We had Alicia (Silverstone) try on this yellow Dolce & Gabbana suit. It was off the rack. I had to pay for it. In the fitting, everyone just went, ‘Yes.’ We’d found THE outfit.

Heckerling: You don’t dress them separately; they were a pair. They had to go together.

May: We wanted Dionne to complement her, so we did the black and white suit. We added the vinyl lapels to match her hat. Amy was such a visionary, to have a girl who was African American in that setting of rich families in Beverly Hills wearing designer clothes.

Amber

May: Amber was a fashion victim and wanted to be Cher so bad. She loved dressing up and themes, so this was her sailor outfit but done in red. A lot of directors don’t let actors wear hats because you can’t see their eyes, but Amy was always saying, ‘What kind of hat can we add to this?’

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Heckerling: Amber was going to be in the classroom, so it was all about the hat.

May: When I put the dollar sign on Amber’s hat, Amy almost cried because it was so perfect. It’s not often that you get to dress a secondary character in such a dynamic way.

Heckerling: The idea with Amber was to have her going to different kinds of characters with her fashion. She didn’t just get up in the morning and say, ‘What should I wear?’ For Amber, it was more like, ‘Who should I be?’

Gym Class

May: Alicia had a beautiful spaghetti-strapped black tank top. The look was new at the time but is still emulated today. Amber wore a striped outfit, like a Mexican wrestler or old bathing suits, and Dionne had a tuxedo shirt. We tried to take things that were high fashion and translated them to the gym.

Heckerling: If I was going to be having these characters wearing different colors to represent seasons. The gym class was going to carry through all of the seasons; I felt it should be consistent, so we went with black and white. It needed to be state of the art fashionable in styles that still reflected each of the characters.

May: All of these styles are very different, but it was my job to make them work. It’s like putting a puzzle together, but we’d always start with Cher’s outfit being at the center.

Chatting with Mr. Hall

May: Cher is in a classic schoolgirl outfit, a little sweater vest, the plaid skirt with knee-highs, a timeless look. She was dressed to look more grown-up, so Mr. Hall saw them as adults, as equals. I loved Wallace Shawn’s look, the ill-fitting tweed jacket that looked like he’d had it for 20 years, and his outdated ties. She’s more together than he is. Then there’s Dionne with the 1950s clutch, the vinyl skirt, the Bouclé sweater. It was a beautiful and effective juxtaposition to Cher. It worked together very well as a color palette.

Tai

May: For Tai, we needed to see her arc, what happened to her and know how she matured. It was imperative to have a lot of room to grow with her. She came from the East Coast and was very much about what was happening on the street, wearing oversized pants and t-shirts. It was youthful and down-to-earth. It was a great way to introduce her.

Heckerling: Fashion for girls like Tai was a t-shirt where you would show what cartoons or movies or bands you liked, and the rest of it was just layers to keep you warm and hid eyour body. At the end of the journey, she’s back to her roots but in an evolved way, wearing different styles of t-shirts with a bit of jewelry, and Tai and Cher agree to be friends because of who they are, not how they looked.

May: Cher’s plaid skirts were designer, but Tai’s were from Contempo Casual. Her style progression reflected her finding herself in her journey of emulating Cher.

“Clueless” celebrates its 25th anniversary with a Blu-ray and a Limited Edition Blu-ray Steelbook release on July 21.

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