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crunchies, cropped baby tees, mismatched earrings—the late 1980s and ’90s aren’t exactly legendary eras for fashion, but the nostalgia-gushing heart wants what it wants. Two set-in-Seattle bastions of the bildungsroman flick, Say Anything and 10 Things I Hate About You, respectively hit their 30- and 20-year anniversaries in 2019. Yet somehow the styles in each are the clothes people are wearing right now. 

Take Say Anything’s Lloyd Dobler. The hopeless romantic, played by a then-ascending John Cusack, favors staples like crew neck sweaters, band tees, and a just-so trench. Lloyd nails his 1980s devil-may-care look with the same unflinching confidence he uses to pursue Diane Court. “The thing about Lloyd is that he had a uniform and he knew how to rock it,” says Ali Brownrigg, who owns Swan Dive Vintage and Consignment in Pioneer Square. Brownrigg, also a former style editor, points to that iconic khaki coat because it both looks objectively great (a flawless fit, nice shade of tan, perfect weight for Seattle weather) and tells a story about his character. “Lloyd is comfortable in his own skin, so anything he wears—even a white shirt with a black skinny tie under a trench coat—looks good on him.”

Teens who flocked to theaters in 1999 to see 10 Things may have pined for younger sister Bianca Stratford’s pink two-piece prom gown or red babydoll minidress. As adults they can appreciate how thoroughly cool older sister Kat Stratford (Julia Stiles) still looks two decades later. The film’s costume designer, Kim Tillman, says that wasn’t a mistake. “The reason the clothes look good is the cast was marching to their own beat,” says Tillman. “I tried to give them classic looks.” Kat, both Betty Friedan–devouring and preternaturally immune to high school drama, paired slouchy ’70s-era army pants with of-the-moment cropped tees or vintage tops (likely happened upon in an underground thrift shop). Her poetic streak hiding beneath a piss-off attitude feels utterly 2019.

These days, movies that take place in Seattle are more cultural outlier than seminal teen flick (hello, 50 Shades of Grey). While the grunge and coffee tropes of bygone decades have mostly waned, our relentless sense of originality remains. Yet another way we’re ahead of our time.

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