Bike Shorts, Dad Sneakers, High Socks—Princess Diana Wore This Summer’s It Items First

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Puffed-sleeve dresses, bike shorts, chunky sneakers—these are just a few of the items you’d find in the #HotGirlSummer starter pack. They also happen to be staples of Princess Diana’s summer wardrobe, lest you forget who made those trends in the first place. Usually the conversation around Lady Di’s style tends to center on her fanciest looks—her Emanuel wedding gown, the dresses she wore to meet heads of state—but today’s It girls are more obsessed with her casual, unstudied looks, likely a result of growing up with athleisure. Hailey Bieber even recreated a few of Diana’s most famous paparazzi photos in a shoot for Vogue Paris, including that infamous sweatshirt, bike short, and sneaker combination. Bieber looks almost eerily similar to the “queen of hearts,” who passed away 22 years ago today, in her modern version of the look; she’s even got her keys in her teeth, just like Diana in the original photo.

Below, we’ve pulled more examples of Diana’s elegant, yet never fussy style, plus a few ways you can get the look. From silky shirt dresses to printed leggings and sensible loafers, they’re items that were relevant then, and feel just as fresh now—and will no doubt come back into fashion again and again.

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Photo: Alamy
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AMUR Bibi pleated handkerchief-hem midi-dress

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Octavia Elizabeth Sapphie Alexis earrings

Roger Vivier satin-clutch envelope flap

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Manolo Blahnik Carolyne pointy-toe slingback pumps

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Photo: Getty
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H&M silk blouse with smocking

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Loro Piana Regent s cashmere sweater

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Erdem Sidney floral-print cotton-blend slim-leg pants

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3DM Lifestyle Belgian loafers

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Photo: Getty
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Valentino floral-print silk crepe de chine midi-dress

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Bottega Veneta Marie leather shoulder bag

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Tabitha Neely espadrille mary janes

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Chopard Happy Sport watch

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Photo: Shutterstock
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Hillflint merino Harvard letter sweater

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Tna Atmosphere bike shorts

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Gucci large vintage canvas shoulder bag

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Krewe Milan sunglasses

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Photo: Shutterstock
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Gucci split mock-neck cashmere sweater

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Raey bias godet silk-satin slip skirt

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Prada pre-owned Tessuto Stampato tote bag

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Gravati flat leather smoking loafers