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This delicious film centers around two evil step-siblings—Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe)—who make a bet: Sebastian must deflower their prep-school headmaster’s daughter (Reese Witherspoon) before the Star wars the mandalorian season 3 art inspired new poster shirt Additionally,I will love this start of term. There’s deception, heartbreak, revenge—plus, the evil Kathryn and her impeccable, ’90s minimalist wardrobe? To die for. —Christian Allaire, fashion and style writer. In my eyes, Jawbreaker is the O.G. Mean Girls. You’re missing out if you’ve never seen this campy, dark-humor classic: Basically, a trio of popular high school girls accidentally murders their best friend—the weapon is jawbreaker shoved down her throat—and then tries to cover it up. Along the way, they wear some seriously killer ’90s fashion. Watch it for this hallway-walk scene alone. —C.A.
I’ve definitely watched 10 Things I Hate About You at least 10 times—okay, more like 100 times. It premiered in 1999, but I didn’t actually see it until a few years later when I was in junior high. My twin sister, best friend, and I became instantly obsessed; as soft-spoken and awkward preteens at a Catholic school in Indianapolis, we aspired to Kat’s sharp-tongued, no-fucks-given attitude—and, of course, we were truly in love with Heath Ledger. So much so that when he died a few years later, we wore head-to-toe black to school. —Emily Farra, senior fashion news writer
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