24 Most Iconic Style Moments of Princess Diana in the 1980s and 1990s

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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. 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.”

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

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

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

A sweater so ugly that it’s cute.

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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