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.
Princess DianaPrincess Diana
Style Moments
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. 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's some of her best off-duty looks from the 1980s and ’90s, proving that she really was “The People’s Princess.”
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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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| 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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| Giving us Fendi Fall 2017 vibes with red accessories back in 1983. |
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| A sweater so ugly that it’s cute. |
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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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| Princess Diana shows her sporty side on a ski holiday in Klosters, Switzerland in February 1986. |
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| Pink gingham and moccasins with Harry at Highgrove on July 18, 1986. |
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| Bed sheet florals in 1986. |
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| The royal family in the gardens of the Highbrow House in July 14, 1986. |
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| Blending in with her surroundings at a Saudi Arabian picnic in 1986. |
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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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| The Princess at the Polo Club wore a “British Lung Foundation” sweatshirt in ’88. |
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| She had a knack for “militant equestrian cool.” |
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| World’s best mom. |
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| A precursor to the Vetements tracksuit moment, while in West Berlin in 1989. |
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| Gracing us with another pastel overall look. |
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| An all leopard look while on holiday in Necker Island in the Caribbean, 1990. |
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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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| It might have been this very graphic tee that earned her the title, “The People’s Princess.” |
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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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| Leaving Chelsea Harbour Club in London in a Virgin Atlantic sweatshirt, 1995. |
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| Khaki pants in check in Angola, 1997. |
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| Master of simplicity. |