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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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)

Blue Eyeliner, Take Two

Here, the Princess matched her eye color to an over-the-top Philip Somerville turban hat during a 1989 visit to Dubai. (Photo: Anwar Hussein/WireImage)

Blue Eyeliner, Take Three

Princess Diana and her baby blues at a state banquet in the Champs-Élysées Palace in Paris, France. (Photo: Tim Graham/Getty Images)

Revenge Dress

Wearing this famous black revenge dress, commissioned from Christina Stambolian, was a spectacular coup by the princess on the very evening that Prince Charles made his notorious adultery admission on television. And she didn’t stop there. … (Photo: Getty Images)

Revenge Dress, Take Two

This post-split red dress by designer Catherine Walker screams, “Moving on without you!” (Photo: Tim Graham/Getty Images)

Revenge Dress, Take Three

Diana really pushed the boundaries with this stunning white Versace dress, both by showing a lot of skin and by wearing an Italian design. (Photo: Tim Graham/Getty Images)

Choker as Headband

This Art Deco–era choker, from Her Majesty’s jewel vault, was a favorite of Diana’s, and she wore it many times. But she really made waves when she wore it as a headpiece. (Photo: Getty Images)

Choker as Headband, Take Two

At a dinner hosted by the Emperor of Japan, Diana wore a royal blue evening dress by designer Yuki and a stunning sapphire-and-diamond headpiece that featured elements taken from a watch. (Photo: Tim Graham/Getty Images)


Before Diana, royals were rarely seen wearing denim in public, let alone overalls. Her down-to-earth mom style endeared her to millions. (Photo: Julian Parker/UK Press via Getty Images)

Overalls, Take Two

This chic shot in white overalls, taken at Diana’s home at Highgrove House, looks like it could have been taken just last week. (Photo: Tim Graham/Getty Images)

Workout Clothes in Public

The Princess of Wales was notoriously fit, and that obviously comes from hard work at the gym. She was never shy — particularly after her separation — about wearing sweatshirts and shorts in public after a workout. (Photo: Anwar Hussein/Getty Images)

Workout Clothes, Take Two

This Virgin Atlantic graphic sweatshirt, orange shorts, and white trainers outfit showed off Diana’s lean legs — a decidedly rule-bending move at the time. (Photo: Anwar Hussein/WireImage)


Diana bucked the frilly princess style by embracing menswear, including ties, button-down shirts, and menswear-style coats. (Photo: Tim Graham/Getty Images)

Menswear, Take Two

While visiting Sandhurst Military Academy in 1987, the Princess played with a military fashion theme. (Photo: Getty Images)

Menswear, Take Three

Later in her life, Diana embraced a more chic verson of androgyny, pairing a tie with a gold-embellished jacket and fitted pants. (Photo: Julian Parker/UK Press via Getty Images)

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