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.