She may be an Upper East Side terror—but Sarah Michelle Gellar’s character has exquisite taste.
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 and hot Sarah Michelle Gellar —who make a spicy bet with each other: Sebastian must deflower their headmaster’s daughter before the end of the year. The plot, however, is really not that important to me.
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.
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