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Blue Eyeliner

Diana, Princess Of Wales’s most stunning attribute may have been her bright blue eyes, and she often played them up with a touch of blue eyeliner and sometimes blue mascara. This might seem a bit tame in our world of extreme makeup tutorials, but at the time it was quite edgy. (Photo: Tim Graham/Getty Images)

How Princess Diana transformed royal style

By not sticking to tradition, Diana, Princess of Wales, earned her place in the pantheon of best-dressed women in history. And it’s a position that has only been more firmly fixed in the two decades since her death, the anniversary of which is Aug. 31.

Her style evolution — from a feather-haired “Sloane Ranger” in frilly, pie-crust blouses and endless pastels to the regal woman who confidently strode in bodycon velvet, athleisure outfits, and glamorous jewels — hinged on what was some major bending of the royal rules of fashion at the time. The princess’s risk-taking moves — such as wearing denim overalls in public (the scandal!) — paved the way for Kate Middleton’s casual-glam mom style.

“Diana often didn’t wear gloves or hats, and was the first female royal to wear trousers to an evening event,” exhibit curator Eleri Lynn told WWD during a walk-through of “Diana: Her Fashion Story,” an exhibition now at Kensington Palace that showcases the most iconic looks Diana wore during public outings, as well as the reasoning behind the outfits.

“She learned the unwritten rules of royal dressing,” Lynn added, “but liked to break them sometimes.”

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