The Style in Kissing Jessica Stein Has the Ultimate Noughties Appeal

Stein and Cooper are yin-and-yang both lifestyle and fashion-wise. And yet, they meet through a classified ad and eventually–spoiler alert–start dating. The film isn’t so much an LGTBQIA+ narrative but more of a coming age story about someone finding themselves. Throughout this, we see two women finding themselves. For Stein, that also includes finding her style.

Take their first date. Cooper is sitting at the bar in a semi-sheer fuchsia top—could it be Gucci?—with a thin matching scarf strung around her neck, super-tight jeans, and stiletto boots. Stein, on the other hand, looks like she’s come out of a Nine West catalog in a stiff grey dress and a cream cardigan. (Later in the film, Cooper refers to her as “the Jewish Sandra Dee.”) After a few drinks, Stein loosens up and so does her wardrobe: her cardigan ever-so-slightly slips off to reveal her dress strap.

KISSING JESSICA STEIN, Heather Juergensen, Jennifer Westfeldt, 2001, TM & Copyright (c) 20th Century Fox Film Corp. All rights reserved.Photo: Courtesy of Everett

Cooper’s style is all the more enviable now, 21 years later. She wears slinky red dresses, a clingy black dress with buttons across body, and shirts that are either searingly bright or printed. Her look feels both real and aspirational. After all, the film’s costume designer Melissa Bruning was shopping where all women shopped pre-9/11: the discount department stores of Century 21 and Daffy’s. “It was great at the time, with all this designer stuff from Europe that people didn’t know what to do with,” she says. Bruning also took inspiration from women she saw in the East Village, and from her own wardrobe. “Part of it was that I dressed that way. I lived around the corner from Saint Mark’s and it was very much an influence of street style,” says Bruning, adding, “I felt like I needed to time capsule Manhattan at that time.”

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