1Topped-Off Teen
Getty ImagesBefore she graduated to elaborate fascinators, Di went with a classic black chapeau in her formative years.
2The Original Normcore
Getty ImagesWe want to wear this now.
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3An Oversized Sweater Over a Dress
Getty ImagesSporting what we'd now call a "boyfriend sweater," Princess Diana makes effortless look chic.
4Tied at the Neck
Getty ImagesSomehow this fair isle sweater, button-up oxford, and ribbon doesn't come across as granny.
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5Turban-Hat Hybrid
Getty ImagesDiana covers her head in an incredibly chic way.
6Stacked Watches
Getty ImagesDiana did the arm party thing before it was even a thing.
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7Gingham Pants
Getty ImagesSummery fancy pants for a polo match. Is there anything more appropriate?
8Initial Necklace
Getty ImagesA classic piece with a hint of fun. We're into the gold hoops, too.
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9Matching the Outfit to the Atmosphere
Getty ImagesThis sunny yellow dress against the bright yellow backdrop makes a stunning combination.
10A Statement Collar
Getty ImagesLeave it to Princess Diana to take a collar to whole new fashion heights.
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11A Menswear-Inspired Fedora
Getty ImagesThis boyish topper balances out the high-necked, feminine shirt.
12The Beret
Getty ImagesA lesson on how to wear a beret without looking like a french painter.
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13Layered Pearls
Getty ImagesShe manages to make pearls on pearls on pearls look chic, not cheesy.
14High-waisted Pants and a Loose Fitting Shirt
Getty ImagesSome of Diana's most casual, laid-back looks are her most stunning.
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15The White Tux
Getty ImagesSuited up, black tie style. Diana stands out in a sea of gray suits.
16Jeweled Headband
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17Overalls
Getty ImagesOveralls are back—but Diana was wearing them almost 30 years ago.
18Peplum Hem
Princess Diana Archive//Getty ImagesThe peplum trend saw a resurgence in the early 2010s, but Diana did it first.
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19Animal Print
Tim Graham//Getty ImagesThis flowy cheetah print dress feels current right now.
20Double Denim
Tim Graham//Getty ImagesA Canadian tuxedo is always perfect for a day out with the children.
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