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This year marks the 30th anniversary of the release of the teen classic Clueless, and the fashion from the 1995 film still looks fresh. According to costume designer Mona May, that’s completely by design.
“Everyone was wearing grunge back then, so there was no blueprint for how to create these costumes. It was really amazing that we were able to create something so fresh,” May told Page Six Style.
“The movie is based on Jane Austen’s ‘Emma,’ and it’s set in Beverly Hills, where all the rich girls have their daddy’s credit cards and can wear whatever they want. I’ve never seen high school kids dress like that.”
Instead of the baggy jeans, flannel shirts, and backwards hats that were mandatory at the time, Cher (Alicia Silverstone), Dionne (Stacey Dash), and their friends wore colorful cardigans, preppy plaid miniskirts, playful hats, and sweet Mary Jane heels with thigh-high stockings.
“We wanted[the wardrobe]to be very girly. An antidote to everything we were seeing in high school at the time. Color and joie de vivre were very important to us. Like, let’s be girls!”
May’s new book, The Fashion of Clueless, is packed with fun facts about the film’s costumes, many of which will surprise even the film’s most ardent fans.
I recently spoke with the designer to get the scoop on some standout information from the book, from the surprising inspiration behind Cher’s digitized closet to how Mae wove “Emma” Easter eggs into her wardrobe.
Cher’s iconic yellow plaid Jean Paul Gaultier suit wasn’t her first choice for the opening scene.
Although May and Clueless director Amy Heckerling agreed that a brightly colored schoolgirl-style skirt suit would perfectly reflect Cher’s “queen bee” status across the quad, blue and red options were considered first.
“When I saw yellow, it just popped into my head. I was surprised. It’s not even a great color for blondes, but I was fascinated,” May told Page Six Style.
“The blue was beautiful, but it wasn’t vibrant. We tried red, but right away Amy Heckerling said, ‘No, this is a Christmas color palette.’ And then yellow comes in.” The moment she put it on, it was like a ray of sunshine. It was perfect and she felt so good. There was no turning back. ”
Many of the costumes in the film were purchased from vintage and thrift stores.
Cher alone changed costumes 63 times throughout the film, as she had “very little money” and had to create hundreds of costumes. — May says she was “very rough” and had to go “high and low.”
Among the standout second-hand styles seen on screen: Dionne’s (Stacey Dash) red vinyl micro miniskirt, leopard-print coat, signature black bag, and Cher’s snap-front suede skirt.
“Even if it comes from a thrift store, modify it. Make it work for you,” May advises. “Even $0.99 items can look really designer when tailored.”
Cher’s computerized closet was inspired by the way Heckerling’s friends cataloged his wine collection.
“She was like, ‘Mona, let’s try it with clothes!'” May recalls Heckerling’s “brilliant” idea to adapt the concept from Vino to Versace. But back in 1995, digitizing your wardrobe was not an easy process.
“I had to catalog the clothes and take pictures of everything. It was an analog era,” May recalls. “We made it happen.”
The cast members’ over-knee socks are inspired by “Cabaret.”
According to May, it was Heckerling’s idea to incorporate thigh-highs throughout the film because “she loves the ’20s.”
Tall stockings were completely unfashionable in the ’90s and were “a little risqué” for a teenage character, but the designer says “it worked.”
The costumes are full of nods to “Emma” and Jane Austen.
Since the film is based on Austen’s 1815 novel, May thoughtfully incorporated Regency-era trends like cap sleeves and Empire waists into her characters’ wardrobes.
Ironically, drawing on silhouettes from the past gave May’s costumes long-term “staying power.”
“We used these timeless shapes,” she recalled, pointing to a pale green dress that was “one of Alicia Silverstone’s favorite outfits,” and featured a flattering A-line cut, puffed sleeves, and a dainty bow just below the bust.
“That (dress) is on a rack somewhere right now.”
Dionne wears a whopping 25 different hats throughout the movie.
Mei’s personal favorite? The Dr. Seuss hat she wears in the first scene, a black and white centerpiece accented with bright red camellias, was designed by New York milliner Corkin.
“It was very Chanel,” she says. “I took the hat to the fitting and I was like, ‘Okay, Stacey, what do you think?’ And she was like, ‘Yeah, baby!’”
May says the key to wearing bold accessories like this is “confidence.”
“When you put someone in this crazy hat, it just looks like a costume, right? But when Stacey Dash puts it on and she comes out of that house in the morning and goes to school with Cher, you think, ‘Okay, this is the coolest thing ever.'” An actor should wear it and create something iconic. ”
May had to beg Alaïa’s team (in French!) to borrow Cher’s famous red dress.
The designer mini costs more than $3,000, a “complete” departure from May’s meager budget.
“We found someone who spoke French, and this was also in the analogue era.[So we]picked up the phone or faxed it, talked to someone there, and said in French, ‘Can I borrow this dress?'” she recalls.
“Back then, we didn’t have a PR machine, we didn’t have people sending us clothes like we do now, and we had creative actors. Nobody knew who[they were],” May continues. “But they agreed.[The late Azzedine Alaia]was a very beautiful person and a really supportive artist. He sent us the dress.”
In discussions with the team, May wisely withheld the fact that Cher would be wearing the dress in the scene where she is forced to the ground at gunpoint in the middle of a parking lot.
“I was like, ‘Alicia, don’t breathe!'” We were basically blowing (dust and dirt) out of the ground. I was like, “I can’t catch you!” I was hyperventilating. ”
The dress was so special that Heckerling decided to write it into the script. Cher famously initially resisted the robber’s orders by saying, “You don’t understand. This is Alaia. He’s like a totally important designer.”
It took “20 or 30” fittings to find Cher’s unforgettable white Calvin Klein dress.
Heckerling’s script only had her character wear something “inappropriate” during her date with Christian (Justin Walker), giving Mae room to experiment.
“Everything we considered[initially]was a little too ‘negligee’ and a little too flesh-toned,” she says. “We tried getting into underwear (area) but it didn’t work out. She’s 16! Everything else looked sexy.”
In contrast, Calvin Klein’s number hit all the right notes, thanks to its stretchy cotton construction (as opposed to satin or lace).
“It wasn’t too tight. And the cream tones were really important, too, because it was innocent and almost wedding-like,” May says.
Alicia Silverstone’s real-life personal style was the exact opposite of her character’s style.
“At that time, she had no interest in clothes at all. She had no interest in them at all,” May recalls. “She was already an activist. She literally came to fittings wearing sweatpants and flip-flops.”
But it was the endless fittings that helped the teen star take on the character of a spoiled Beverly Hills student.
“As an actor, you have to go through this process to get to know yourself as the character,” May says. “And she learned! Alicia started wearing clothes and figured out how to walk, flip her hair, and be Cher. The costumes teach that so much.”
Meanwhile, Paul Rudd wore his own clothes on screen as Josh.
Rudd had much more in common with his character than with Silverstone, and many of his costumes included items from his own closet, from boots to Amnesty International T-shirts to University of Kansas hats.
“He was just that guy!” May says. “We ended up making fun T-shirts with him that kind of told the world who he was. There were breast cancer awareness T-shirts that were very popular at the time, and my ex-boyfriend gave me a T-shirt from a cool underground club in Austin. Those are clues about (Josh’s) personality.”
Cher’s glittery hair clip later appeared in another popular teen movie.
May’s new book reveals that 10 years after Clueless, hairstylist Nina Paskowitz repurposed Cher’s exact rhinestone hair tie on Amanda Bynes during production of 2006’s She’s the Man.
“Amanda loves Clueless and was so excited!” Paskowitz recalls.
Added May: “It’s just crazy how[Clueless]continues to live on.”
Miss Geist (handsome Caplan) could not sit or eat in her wedding dress.
The film’s finale sees Miss Geist marry her fellow teacher, Mr. Hall (Wallace Shawn), and May said Caplan requested a bridal look that took full advantage of her “petite, perfect body.”
“She wanted something with a high collar, an open back[and]a close fit,” says the costume designer, who designed the gown herself.
The only problem was that Caplan couldn’t sit second-skin style. So May bought a tilt board, like the one used by Jean Harlow, Katharine Hepburn, and Judy Garland during Hollywood’s Golden Age, so she could rest between takes.
“And I didn’t feed her at all,” she added.
Amy Heckerling and Mona Mae both have cameos in the film.
Heckerling plays a bridesmaid at the wedding of Miss Geist and Mr. Hall, wearing a matching pastel pink outfit as Cher (designed by May). If you look closely, you can see that she is struggling to catch the bouquet. Meanwhile, the costume expert makes a brief appearance as Cher’s masseuse.
May says of her relationship with Silverstone: “It’s been great because we’ve become close.” “It was very comfortable for Alicia, and Amy was like, ‘You have an accent!'” I fit the role perfectly as an Eastern European. ”
This interview has been edited for length and clarity.
