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 stepsiblings—a hot Ryan Phillippe (Sebastian) and hot Sarah Michelle Gellar (Kathryn)—who make a spicy bet with each other: Sebastian must deflower their headmaster’s daughter (Reese Witherspoon) before the end of the year. The plot, however, is really not that important to me. More than 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 façade, you’d never suspect she’s actually a total bad girl with actual cruel intentions. She slinks about her parents’ Upper East Side town house 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 skintight corset underneath. You know, casual lounging-around-at-home clothes.
Kathryn’s elegant clothes are seemingly meant to juxtapose her inner mean girl in the film. In one monologue, for instance, she wears a pretty floral day frock while declaring, “I’m the Marcia fucking Brady of the Upper East Side, and sometimes I want to kill myself.” There’s a sweetness—yet toughness—to the way she throws things together. My favorite outfit is the sheer icy blue top and leather skirt she wears in her bedroom, which—for some reason—has deep blue walls with ornate crown moldings. The look exudes the clean minimalism of the ’90s but would still appear modern today.
Twenty-five years later, though, my real respect for the movie’s fashions lies in Kathryn’s luxurious style being pulled off with miniscule funds. “We had a very small budget, so we had to be really creative with the looks,” Wingate recently told CNN. You’d never guess it: Kathryn simply looks rich at all times. It’s also fun to imagine what Kathryn would wear if she were terrorizing her private school in 2024. She would definitely wear the stealth-wealth pieces from discreet labels like Phoebe Philo and The Row. You know the kind of clothes we’re talking about: a simple cashmere sweater that costs a small-car payment. Because if Kathryn’s going to do one thing, it’s make being bad look good.
