The Final Word On What Cher, Dionne & Amber Would Dress Like Today

Illustrated by Sydney Hass.
If you grew up in the '90s, chances are the outfits in Clueless are etched into your memory. Whether the film spurred some adventurous looks (furry backpacks and marabou-feather pens?) or led you to copy entire outfits (Cher’s capable-looking driving-test ensemble, anyone?), you owe a debt to costume designer Mona May, the woman responsible for bringing us all of the classic Clueless looks we’re still obsessed with two decades later.

May describes being a costume designer as being both a “psychologist and a detective,” especially when it came to Cher’s 60 outfit changes. “It’s a lot of work, fitting the whole puzzle together. A lot of thinking goes on with it, and it’s really fun.” She believes what made Clueless so important back then — and why it remains relevant now — is that the movie never “felt vulgar.” It invoked a certain fun, girly innocence that May says is rare in fashion. As for that upcoming Clueless musical? Get excited, because again, May will be behind the seams. “It’s exciting because it’s a whole other medium," she adds, "so it’s very different. There are quick changes, different sets.”

To celebrate the film's 20th anniversary, we asked May to reimagine the cast in modern-day clothes and trends — and dress Cher and the gang in the looks they would wear if Clueless were made today.

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Illustrated by Sydney Hass.
Cher
The Erin Fetherston dress is really cute for Cher. For her purse, she’d need something dainty like the Chloé Mini Marcie. She wouldn’t have a big bag. This is something that she’d definitely go for.”
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Illustrated by Sydney Hass.
Dionne
"With Dionne, we go a lot more sassy. The yellow-and-black House of Holland outfit is great with the Philip Treacy hat.”

House of Holland, fall 2015 top and shirt.
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Illustrated by Sydney Hass.
Amber
"The Fendi sweater is hilarious. Amber would also be very into Jeremy Scott.”
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Illustrated by Sydney Hass.
Tai
"Tai was more innocent and shy in a way. She was still very young compared to the other girls, and not as wordly. Her clothes had to represent more of that. She wanted to emulate the girls, but her [look] was more from the mall, [whereas] the other girls' were more high-end. The flannel Madewell outfit is more her thing because it’s kind of shapeless.”

Madewell fall 2015 plaid scarf, sweater, skirt.
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Illustrated by Sydney Hass.
Murray
"2015 Murray is a bit more sophisticated, but everything he wore was untucked and kind of messy.”

Kanye West for Adidas pants.
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