Creating Cher's Iconic 'Clueless' Looks

This Friday marks the 20th anniversary of Clueless, the ’90s cult classic that is beloved as much for its heroine’s candy-colored, rotating closet as it is for its teenspeak and quotable one-liners.

The film put Alicia Silverstone on the map as Cher Horowitz, a shallow-brained Beverly Hills teen queen with a heart as big as her wardrobe.

Writer and director Amy Heckerling “deserves snaps,” as Cher would say, for her clever satire of California rich kids in the mid-’90s and for successfully adapting Jane Austen’s Emma into a contemporary comedy that still resonates two decades later.

Indeed, the film’s enduring appeal lies in its witty dialogue and eccentric but timeless feminine fashion that ushered in a departure from ’90s grunge.

“Amy and I went to high schools in Los Angeles to see what the kids were wearing and the girls didn’t look any different from the boys,” Clueless costume designer Mona May tells The Daily Beast. “They all wore baggy pants and plaid shirts, and we really wanted to give Cher and the girls a sweet, fun, fashion-forward look.”

May mixed contemporary runway styles (crop tops and babydoll dresses) with classic looks from the ’60s and ’70s (A-line skirts worn with knee-high socks and Mary Janes).

The yellow plaid miniskirt and matching blazer from Dolce & Gabbana that Cher wears on her first day of school was a high fashion version of the Catholic schoolgirl uniform.

“I was just reinventing something that was already in our consciousness,” says May, who was born in India but grew up in Poland and Germany before moving to the U.S. in her early 20s. “It was about taking the classics to a new level while making sure each girl’s outfit was consistent with her character.”

For Cher, a perfectionist whose shopping addiction rivals Carrie Bradshaw’s, that meant lots of matching schoolgirl ensembles and ultra-feminine, occasionally over-the-top outfits, like the red Alaia dress and maroon jacket with black marabou trim she wears to the party in the Valley.

She looks fantastically out of place among throngs of skater boys like Travis Birkenstock (the name says it all), and has a conniption fit when he spills beer on her Jimmy Choos (“Ruin my red satin shoes why don’t you!”).

Even when a man points a gun at her head and tells her to lie face down on the ground, Cher pleads with him—rather hilariously—to spare her dress. “It’s like a totally important designer.”

Like Austen’s heroine, Cher is at once annoyingly entitled and endearingly naive; a spoiled, self-absorbed brat one minute and a caring, vulnerable teenage girl the next.

She is as relentlessly materialistic as she is tirelessly dedicated to matchmaking and helping others. “God, this woman is screaming for a makeover!” Cher says of her frumpy teacher. “I’m her only hope.”

Cher’s best friend Dionne is “wild and sassy and sexier than Cher,” says May, “so we put her in lots of colorful vinyl miniskirts, leopard prints, and quirky hats,” from a black-and-white top hat to a white crochet beanie.

But May was careful that Dionne’s style never veered into caricature territory (the most ridiculous outfits were reserved for Amber).

“I could never go too crazy with Cher because Dionne had to look more wild, so it was always this balancing act,” May tells me, even more so when Tai enters the picture, having been made over by Cher and ditched her oversized jeans and Vans.

“The three of them are in almost every scene together, so we had to make sure what they wore was true to the script,” says May, who put Tai in cheap fabrics to illustrate her middle-class background. “She didn’t have the money to get what Cher got in Paris, so she got the same look at Contempo Casual.”

May also ensured that Cher’s clothes served as character development throughout the movie, like the “most capable-looking outfit” Cher is determined to wear her to her driver’s license test.

She has a tantrum when she can’t find a crucial separate (“Where’s my white collarless shirt from Fred Segal!”), stomping her silver Mary Janes on her bedroom floor and snapping at the maid for sending it to the cleaners.

Later, while clipping stop signs and narrowly avoiding a biker during her test, Cher feels “an overwhelming sense of ickiness.”

The outfit May chose for this scene—a sheer, chiffon tuxedo shirt layered over a tank and paired with an argyle silver skirt—had to “serve a purpose of emotional journey for Cher,” she says. “It was supposed to be the perfect outfit for her driving test but it also had to work for when she unravels afterwards, so we went with chiffon because it wrinkles easily. The whole ensemble was very soft-looking to show her vulnerability.”

After Cher realizes she’s in love with Josh, her philanthropic stepbrother, and throws herself into being “captain of the Pismo Beach disaster relief,” her clothes are simpler and more girly: a pink tank worn over a white T-shirt, for example, while nervously watching CNN with Josh. (When he remarks that she looks “confused,” Cher earnestly delivers a particularly funny line of self-parody: “It’s just that I thought they declared peace in the Middle East.”)

“We wanted her to look less preoccupied with herself, which would mean less time in front of the mirror and more time thinking of others,” says May. “It was subtle, but it was still there.”

Another reason Mary Janes and chunky platforms feature prominently in the film: May thought stilettos would look too “slutty” on teenage girls. There’s hardly any cleavage or provocative displays of flesh in Clueless.

Cher was meant to look “seductive, but not like a sexpot,” says May. She’s a virgin, after all. (“You see how picky I am about my shoes, and they only go on my feet!” Cher tells Tai.)

“That kind of fresh sexiness is missing in our culture,” May adds. “And I think that’s a kind of style expression that we don’t often see in real life.”

Re-watching the film recently, May was shocked to see how contemporary the clothes look. “Some of it looks like Alexander Wang!” (Wang, incidentally, once said Clueless was his favorite film.)

More than anything else, May is proud of the movie’s influence on women.

“Every woman I meet, across generations, has a story about buying or making clothes that looked like something from Cher’s closet. Amy and I really wanted to emphasize feminine sexuality and sweetness when dressing the girls. And I’m so glad we did, because people didn’t just want to emulate them, they actually found themselves in these girls. That’s the greatest gift for me.”