Clueless (1995), directed by Amy Heckerling, is a smart, vibrant reimagining of Jane Austen’s Emma, seamlessly blending classic literature with the slang-filled, sun-soaked world of 1990s Beverly Hills. Heckerling approached the script with intention and literary grounding (she read Austen’s Emma as part of her preparation) and used its structure as the foundation for the film. Her vision was to portray teenage girls as intelligent, complex, and emotionally nuanced, while also adding humor to the stereotype of the fashion-obsessed teen, such as Cher Horowitz.
In Clueless, Cher Horowitz, a stylish, privileged high schooler, takes on the modern role of Emma Woodhouse. Like Emma, she is a self-assured matchmaker who often misjudges those around her, but gradually develops emotional maturity and self-awareness. The film mirrors the social world of Austen’s English countryside by transposing it into the upper-class enclaves of Los Angeles: prep schools, Rodeo Drive, and extravagant Malibu parties replace stately homes and garden walks.
The film’s themes are class, identity, romantic confusion, and personal growth, align closely with Austen’s original, but are reframed through a modern lens. One of the most lasting elements of Clueless is its costume design by Mona May, whose colorful, playful take on teen fashion helped define the decade. Drawing from 1960s mod and 1970s prep, May created looks that felt both nostalgic and cutting-edge. Cher’s iconic computerized closet, in particular, became a pop culture landmark—celebrated for its novelty and foresight, even though no real-life version has ever quite matched its charm.
By combining Austen’s sharp social commentary with the energy of 1990s youth culture, Heckerling captured a generation and gave the world a teen comedy with both brains and style.
Clueless (1995), directed by Amy Heckerling, Alicia Silverstone, Stacey Dash, Brittany Murphy. Costume Design by Mona May
Clueless (1995)
“Wasn’t my mom a Betty? She died when I was just a baby. A fluke accident during a routine liposuction. I don’t remember her, but I like to pretend she still watches over me.” - Cher Horowitz
Yellow Doen Cardigan , Yellow Plaid Elderstatesman Skirt
Alicia Silverstone Clueless (1995)
Gucci Pink Suede Horsebit Sling Bag, White Tennis Dress
Alicia Silverstone in Clueless (1995)
Black Bottega Eye Glasses, Vintage Green Beaded BlueMarine Cardigan, Green Leather Sandals, Green Satin A.L.C green crinkled skirt, Green Gucci Bag
Alicia Silverstone in Clueless (1995)
TWP White Bustier Top, Prada Purple Enamel Rose Pin
“Well, some teachers are trying to lowball me, Daddy. And I know how you say, “Never accept a first offer,” so I figure these grades are just a jumping-off point to start negotiations.” - Cher Horowitz
Charvet Yellow Shirt, YSL 90’s Gold Blazer, Gold Celine Sunglasses, Lili Claspe Shell Earrings, Saint Laurent Mini Pochon Satin Top-Handle Bag
Paul Rudd and Alicia Silverstone in Clueless (1995)
High Sport Red Sweater, Manolo Blahnik Mesh Flats, Mango Sheer Black Dress, Vintage Gucci Embroidered Bag, Rose Fabric Pin
Elisa Donovan in Clueless (1995)
Gigi Burris Ostriched Feathered Hat, Cult Mia Ostriched Feathered Jacket, LaMarqueFreya Strapless Feather-Trim Midi Dress, Vintage Prada Clutch, Miu Miu Black Feathered Bag
Clueless (1995)
Hermes Kitchu Ballet Flats in Black, Hermes Kitchu Ballet Flats in White, Agnes B Striped Shirt
HeAlicia Silverstone and Stacey Dash in Clueless (1995)
Santorini Linen Short Dress, Aeyde Black Uma Ballerina Flats, Sophie Buhai White Oversized Bow Hair Clip, Sandy Liang Socks
Stacey Dash in Clueless (1995)
Hermes Green Bag, Doen Green Cardigan, Doen Green Shell, Ancient Greek Green Satin Clogs, Lie Studio Green Earrings, Prada Straw Crochet Hat
Christian: Do you like Billie Holiday?
Cher Horowitz: I love him.
Vintage YSL Fuschia Bag, Dries Van Noten Fuschia Trousers
“You don’t understand, this is an Alaïa!” - Cher Horowitz
Tweed Chanel Brooche, Vintage Chanel Red earrings, Manolo Blanik Red Heels, Mango red chiffon Dress, BENILDA JACKET Creme Brown Pinstripe
Clueless (1995)
Bottega Red & Pink Flower Earrings, Green Gucci Mary Janes, Mango Floral Dress, Miu Miu Green Suede Bucket Bag, Bode Striped Hair Clip, Marte Ferri Maroon Belt
Stacey Dash in Clueless (1995)
Loro Piana cashmere-blend crochet bucket hat, Vintage Fendi Rattan Baguette Bag
Alicia Silverstone in Clueless (1995)
Rochas Beaded Floral Earrings, Lele Sadoughi. Aqua Crystal Open Weave Bucket Hat
Alicia Silverstone, Clueless (1995)
Khaite Jeans, Vintage Bluemarine Cardigan, Prada Floral Hair Clip, Chanel Mules
Alicia Silverstone in Clueless (1995)
Guest in Residence Shorts, Cream 1960's Purse, Silk shirt with fringed pocket square, Chanel 2023 interlocking flats, Calzedonia white knee-high socks
Alicia Silverstone and Stacey Dash in Clueless (1995)
Green Prada Suede Jacket, YSL Mini red leather shoulder bag
Stacey Dash in Clueless (1995)
YSL eyeglasses, Mango high-waisted Jean Shorts, Sylvie Fleury Flame Cashmere Sweater, Vintage Gucci Raffia Bag, Simone Rocha Flared Sheer Tulle Midi Skirt, Damson Madder Baby Aubrey Quilted Coat
“No, she's a fulll-on Monet. It's like a painting, see? From far away, it's OK, but up close, it's a big old mess.” - Cher Horowotiz
Ruslan Baginskiy white hat, Damson Madder Red Sailor Blouse, Sandy Liang Red Pleated Skirt, Vintage Wedgwood Anchor Brooch, Manolo Blahnik Red Ginham Ballet Flats
“That’s Ren and Stimpy. They’re way existential” - Cher Horowotiz
Prada Hyper Matte Pink Lipstick, Charlotte Tillbury Pink Lip Liner
Hey Mirrin, I shared this story with Mona May who was especially delighted that you used the massage picture because she played the masseuse. xo Jane