13 things you never knew about ‘Clueless’ fashion, from costume designer Mona May


This year marks the 30th anniversary of teen classic “Clueless,” but the 1995 film’s fashion still looks as fresh as ever. And according to costume designer Mona May, that’s, like, totally by design.

“At the time, everybody was wearing grunge. So I didn’t have a blueprint for how to make these costumes. It was pretty amazing that we were able to create something so fresh,” May tells Page Six Style.

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“The film was based on ‘Emma’ by Jane Austen, but [set] in Beverly Hills with all the rich girls having Daddy’s credit cards, being able to wear whatever they want. You’d never seen high school students dressed like this.”

Mona May’s new book, “The Fashion of Clueless,” is full of never-before-seen photos of the film’s costumes and cast. Insight Editions

In place of the baggy jeans, flannel shirts and backwards caps that were de rigueur at the time, Cher (Alicia Silverstone), Dionne (Stacey Dash) and their cohort were clad in colorful cardigans, preppy plaid miniskirts, playful hats and sweet Mary Jane heels styled with thigh-high stockings.

“We wanted [the wardrobe] to be very girly — the antidote to all the stuff we were seeing in high schools 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 movie’s costumes — many of which will surprise even the most diehard fans of the flick.

Illustration of the book cover for "The fashion of Clueless" by Mona May, featuring a yellow plaid pattern with a black clothing tag and safety pin.
Amazon

I recently sat down with the designer to get the scoop on some standout tidbits from the tome, from the surprising inspiration behind Cher’s digitized closet to the way May wove “Emma” Easter eggs into the wardrobe.

“I saw the yellow and it just popped. It took me by surprise; it’s not even a great color for blondes, but I was mesmerized,” May tells Page Six Style. Insight Editions

Cher’s iconic yellow plaid Jean Paul Gaultier suit wasn’t the first choice for the opening scene.

While May and “Clueless” director Amy Heckerling agreed that a brightly colored, schoolgirl-style skirt suit would perfectly reflect Cher’s “queen bee” status as she heads across the quad, blue and red options were considered first.

“I saw the yellow and it just popped. It took me by surprise; it’s not even a great color for blondes, but I was mesmerized,” May tells Page Six Style.

“The blue one was beautiful, but didn’t have the oomph. We tried the red one; immediately, Amy Heckerling goes, ‘No. This is a Christmas color palette.’ And then here comes the yellow. The moment she put it on, it was like a ray of sunshine. It was perfect, and she felt so good in it. There was no going back.”

Both Cher’s skirt and Dionne’s bag in this scene were thrifted finds. © Paramount/ Courtesy: Everett Collection

Many of the movie’s clothes came from vintage and thrift stores.

Since she had “little money” to work with and hundreds of costumes to create — Cher alone has 63 outfit changes throughout the film! — May says she had to be “very scrappy” and “go high and low.”

Among the standout secondhand styles seen onscreen? Dionne’s (Stacey Dash) red vinyl micro-miniskirt, leopard coat and signature black bag, along with Cher’s snap-front suede skirt.

“Even if it comes from a thrift store, alter it. Make it work it for you,” May advises. “Even the $0.99 pieces really look designer when they are tailored.”

In the years since “Clueless” took the fashion world by storm, countless apps and websites have tried to replicate the look and feel of Cher’s digitized closet. ©Paramount/Courtesy Everett Collection

Cher’s computerized closet was inspired by how a friend of Heckerling’s catalogued his wine collection.

“She was like, ‘Mona, let’s do it with clothes!’” May recalls of Heckerling’s “brilliant” idea of adapting the concept from vino to Versace. But in 1995, digitizing a wardrobe wasn’t the easiest process.

“We had to catalog the clothes, take all the pictures. These were analog times!” May recalls. “We made it happen.”

May drew inspiration from multiple decades when creating her “Clueless” costumes; Cher’s signature high socks were straight out of the ’20s. ©Paramount/Courtesy Everett Collection

The cast’s over-the-knee socks were inspired by “Cabaret.”

It was Heckerling’s idea to incorporate the thigh-highs throughout the flick, according to May: “She loves the ’20s.”

While tall stockings weren’t trendy whatsoever in the ’90s and “a little risqué” for the teenage characters, the designer says, “it worked.”

May recalls that this puff-sleeved, empire-waisted green dress was “one of Alicia Silverstone’s favorite outfits.” CBS via Getty Images

Nods to “Emma” and Jane Austen abound in the costumes.

Since Austen’s 1815 novel provided the film’s source material, May thoughtfully wove Regency-era trends like cap sleeves and empire waists into the characters’ wardrobes.

Ironically, drawing on silhouettes of the past helped give May’s costumes “staying power” in the long run.

“I used these timeless shapes,” she recalls, pointing to a pale green dress that was “one of Alicia Silverstone’s favorite outfits” and featured a flattering A-line cut, puff sleeves and a dainty bow just below the bust.

“That [dress] is on the racks somewhere right now.”

“Been shopping with Dr. Seuss?” Cher asks Dionne upon clocking her kooky black-and-white hat. ©Paramount/Courtesy Everett Collection

Dionne wears a whopping 25 different hats throughout the film.

May’s personal favorite? The “Dr. Seuss hat” she sports in her first scene, a black-and-white showstopper punctuated with a bright red camellia and designed by NYC milliner Kokin.

“It was so Chanel,” she says. “I brought that hat to the fitting and I was like, ‘OK, Stacey, what do you think?’ And she was like, ‘Yeah, baby!’”

May says the key to pulling off such a bold accessory is “about the confidence.”

“You can have someone wear this crazy hat and it just looks like a costume, right? But then Stacey Dash puts it on and when she comes out of that house in the morning to go to school with Cher, you’re like, ‘OK, this is the coolest thing ever.’ It takes the actor to wear it and to create something that iconic.”

Cher’s red Alaïa dress was such a pivotal fashion find, Heckerling wound up writing it into the movie’s script. © Paramount Pictures/ Courtesy: Everett Collection

May had to beg the Alaïa team (in French!) to let her borrow Cher’s famous red dress.

The designer mini cost more than $3,000, putting it “completely” out of May’s shoestring budget.

“We found somebody who speaks French — again, analog times, [so we had to] pick up the phone or fax, talk to somebody there, ask them in French, ‘Can we please borrow this dress?’” she remembers.

“There was no PR machine, no people sending you clothes like they do now, and also we had ingenue actors — nobody knew who [they] were,” May continues. “But they agreed. [The late Azzedine Alaïa] was such a beautiful man; a really supportive artist. He sent us the dress.”

During her talks with the team, May wisely withheld the fact that Cher would be wearing the dress during a scene in which she’s held up at gunpoint and forced to get down on the ground in the middle of a parking lot.

“I was like, ‘Alicia, don’t breathe!’ We were basically blowing [the dust and dirt] off the ground. I was like, ‘We can’t snag it!’ I was hyperventilating.”

The dress was so special, Heckerling wound up writing it into the script; Cher famously resists her mugger’s commands at first, telling him, “You don’t understand: This is an Alaïa! He’s, like, a totally important designer.”

Cher’s father (played by Dan Hedaya) memorably tells his daughter her Calvin Klein mini “looks like underwear,” demanding that she “put something over it.” (She complies — kind of — by layering a completely sheer Anna Sui duster on top.) ©Paramount/Courtesy Everett Collection

It took “20 or 30” fittings to find Cher’s unforgettable white Calvin Klein dress.

Heckerling’s script simply called for the character to be wearing “something inappropriate” during her date with Christian (Justin Walker), giving May room to experiment.

“Everything that we considered [at first] was a little bit too ‘négligée,’ a little bit too skin-toned,” she says. “We went into the undergarment [realm] and it just didn’t work — she’s 16! Everything else looked too sexy.”

With its stretchy cotton (rather than satin or lace) construction, by contrast, the Calvin Klein number hit all the right notes.

“It wasn’t too tight. And the cream tone was really important too, because it was kind of innocent, almost a little wedding-like,” May notes.

Silverstone sorts through her character’s wardrobe with Heckerling, notably dressed in comfier and more casual clothes than Cher’s. ©Paramount/Courtesy Everett Collection

Alicia Silverstone’s real-life personal style was the polar opposite of her character’s.

“At the time, she was not into clothes — completely not into it at all,” May recalls. “She was already an activist. She was literally in her sweatpants and her flip-flops coming to fittings.”

It was the endless fittings, however, that helped the teenage star get into character as a spoiled Beverly Hills student.

“As an actor, you have to go through this process to learn who you are as the character,” May notes. “And she learned! Alicia started wearing the clothes, understanding how to walk, to flip the hair, to be Cher. Costume informs that so much.”

Paul Rudd brought his own wardrobe to set, including this Amnesty International tee. CBS via Getty Images

Paul Rudd, meanwhile, wore his own clothes onscreen as Josh.

Rudd had far more in common with his character than Silverstone did, and many of his costumes included pieces from his own closet — from boots to an Amnesty International T-shirt to a Kansas University cap.

“He was just that guy!” May says. “We got to do the fun T-shirts with him, kind of telling the world who he is: the breast cancer awareness T-shirt that was so popular at the time, and my ex-boyfriend gave me a T-shirt of some cool underground club in Austin. Those are the clues about [Josh’s] personality.”

Years after Cher wore this rhinestone barrette, it got a second onscreen moment. ©Paramount/Courtesy Everett Collection

Cher’s sparkly hair clip later wound up in another beloved teen movie.

May’s new book reveals that a decade after “Clueless,” hairstylist Nina Paskowitz reused Cher’s exact rhinestone barrette on Amanda Bynes while working on 2006’s “She’s the Man.”

“Amanda loved ‘Clueless’ and was so excited!” Paskowitz recalls.

Adds May: “It’s so crazy, how [‘Clueless’] lives on.”

Cher, Dionne and Tai (Brittany Murphy) plan their future bridal looks during Miss Geist and Mr. Hall’s wedding. ©Paramount/Courtesy Everett Collection

Miss Geist (Twink Caplan) couldn’t sit down — or eat — in her wedding dress.

The movie’s finale sees Miss Geist marrying fellow teacher Mr. Hall (Wallace Shawn), and May says Caplan requested a bridal look that made the most of her “petite, perfect body.”

“She wanted [something] super fitted with a high collar and open [back],” says the costume designer, who designed the gown herself.

The only problem was, Caplan couldn’t sit down in the second-skin style. So help her rest in between takes, May procured a slant board like the ones used by Jean Harlow, Katharine Hepburn and Judy Garland during Hollywood’s Golden Age.

“And I did not allow her to eat at all,” she adds.

Mona May appears as Cher’s masseuse in a scene from the film. CBS via Getty Images

Both Amy Heckerling and Mona May make cameos in the movie.

Heckerling plays a bridesmaid in Miss Geist and Mr. Hall’s wedding, wearing a pastel pink outfit that matches Cher’s (designed by May); watch closely, and you can see her fighting to catch the bouquet. The costume whiz, meanwhile, appears briefly as Cher’s masseuse.

“It was great, because we became close,” May says of her relationship with Silverstone. “It was very comfortable for Alicia. And Amy was like, ‘You have the accent!’ I fit the role [as an] Eastern European.”

This interview has been edited for length and clarity.


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