From Clueless to Heathers: Cool Riffs on Classic Prep

Photos c/o Pinterest: Heathers, The Royal Tenenbaums, Clueless, Annie Hall

From the hallowed halls of the East Coast Ivies to the shores of rowing regattas, preppy style has long been a tried-and-true classic. But if you’re thinking crested blazers and lobster-embroidered chinos have lost their charm, it’s time to turn to a new source of inspiration: the movies. We’ve tapped the wardrobes of four of our favorite atypical heroines, ahead of their time when it comes to putting a fresh spin on the all-American look.

In Heathers, Winona Ryder’s Veronica Sawyer and her hated clique of friends take proportions to the extreme (hey, it was the ’80s), dressed in high-impact blazers and menswear-approved tartans and tweeds. Gwyneth Paltrow’s jaded Margot Tenenbaum serves up a unique slant on sporty-chic attire by mixing stark kohl eyeliner, girlish barrettes, and striped Lacoste polo dresses. For Clueless It girl Cher Horowitz, it’s all about a futuristic dream closet filled with shrunken plaid suiting, sheer white knee socks, and precision-cropped knits. Last but not least? Diane Keaton’s iconic Annie Hall, who basically started an androgynous-chic revolution in roomy trousers, Charlie Chaplin waistcoats, and polka dot neckties.

So before you ship off to Deerfield Academy for tips on wearing madras like a pro, take in a screening of these cultish flicks for a few fashion how-tos, and stock up on some of our quirky takes on the timeless trend — on sale tomorrow.

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