Princess Diana’s Best Casual Looks

Fashion


When you think of Princess Diana’s most iconic fashion moments, there’s the little black dress by Greek designer Christina Stambolian, countless gowns by Bruce Oldfield, or her famous Chopard sapphire choker. To this today, we’re still finding reasons to return to her unrivaled sartorial choices, and there really is no one who has done it better. (Sorry, Kate.)

So what puts her in a different league from other royals and red carpet regulars? The heavily photographed Princess’s true sense of style comes through when she’s looking her most comfortable, the most like herself. Here, we round up some of her best off-duty looks from the ’80s and ’90s, proving that she really was “The People’s Princess.”

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The Princess at the Polo Club wore a “British Lung Foundation” sweatshirt in ’88.

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An ugly sweater moment at Craigowan Lodge on the Balmoral Estate in Scotland, before the engaged couple’s wedding in 1981.

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Princess Diana shows her sporty side on a ski holiday in Klosters, Switzerland in February 1986.

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Pulling off pastel overalls couldn’t have been easy in the ’80s, but here she is at Windsor Great Park in 1981.

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Bed sheet florals in 1986.

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Leaving Chelsea Harbour Club in London in a Virgin Atlantic sweatshirt, 1995.

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The royal family in the gardens of the Highbrow House in July 14, 1986.

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Perhaps the source of inspiration for Demna Gvsalia’s Spring 2017 palette. The Princess exits the Royal Yacht Britannia in Aberdeen in 1985.

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Another polo match, another wallpaper floral in 1985.

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Khaki pants in check in Angola, 1997.

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Giving us Fendi Fall 2017 vibes with red accessories back in 1983.

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An all leopard look while on holiday in Necker Island in the Caribbean, 1990.

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A precursor to the Vetements tracksuit moment, while in West Berlin in 1989.

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While on holiday in Austria in ’94, she was head of her time in a puffy coat that could be Balenciaga Fall Winter ’18.

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Blending in with her surroundings at a Saudi Arabian picnic in 1986.

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Gracing us with another pastel overall look.

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A sweater so ugly that it’s cute.

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Don’t even try to test this woman’s ugly sweater game. Leaving Aberdeen Airport with her Princes in 1986.

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She had a knack for “militant equestrian cool.”

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It might have been this very graphic tee that earned her the title, “The People’s Princess.”

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When the shoes match the skirt. The Princess accompanies Prince Charles to the hospital on her birthday, July 1, 1990.

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