Can you believe it’s been 25 years since Cruel Intentions came out? I certainly cannot! It’s one of my all-time favorite movies from the late ’90s. If you’ve never seen the cult-classic film, it follows two Upper East Side step-siblings—a hot Ryan Phillippe (Sebastian), and hot Sarah Michelle Gellar (Kathryn)—who make a spicy bet with each other: Sebastian (Phillippe) must deflower their headmaster’s daughter (Reese Witherspoon) before the end of the year. The plot, however, is really not that important to me. Over two decades later, it’s Kathryn’s incredibly chic wardrobe that has me rewatching it again and again. And again.
Costume designed by Denise Wingate, Kathryn embodies tasteful uptown style throughout the movie—so much so that, underneath her glossy facade, you’d never suspect she’s actually a total bad girl with actual cruel intentions. She slinks about her parents’s Upper East Side townhouse in smart, tasteful designs by labels such as Donna Karan, Gucci, and Calvin Klein. One of her best looks in the film is worn while making her devious wager with Sebastian: She sports a sleek black Dolce & Gabbana suit with a custom skin-tight corset underneath it. You know, casual lounging-around-at-home clothes.
CRUEL INTENTIONS, Sarah Michelle Gellar, 1999Photo: Courtesy of Everett Collection
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