The Crown: How Princess Diana went from frumpy to fashion icon thanks to Dior and Versace, sparking both office wear and athleisure trends that still inspire chic celebrities like Hailey Bieber

Nov 17 , 2023

Princess Diana’s style took a major turn after she divorced Charles. In 1994 she made headlines with the “revenge dress” (pictured left), which she wore at a party in London. Photos: Tim Graham Photo Library via Getty Images and Martin Keene, AP.

The late Princess of Wales truly found her style in the 90s, trading tartan suits and maternity dresses for beautiful blazers, straight-leg jeans and loafers that still strike a chord today

Post-divorce, Diana courted A-list designers like Gianni Versace and Jacques Azagury, and snared John Galliano’s first-ever design for Dior in ‘the greatest publicity coup in fashion history’

When Lady Diana Spencer married Prince Charles in 1981, she was a self-confessed “mucky pup” who claimed she had only “one long dress, one silk shirt and one smart pair of shoes” in her wardrobe. By the time she died in 1997, she was not simply stylish, but was the most famous clotheshorse in the world and an icon of late 20th century glamour.

As Netflix gears up to release its sixth and final season of The Crown this month, viewers are in for a fashion treat. While 80s Di was undeniably influential – those tartan suits, big-collared pregnancy dresses and outsize shoulder pads were copied around the world – it was in the 90s that she found a fashion formula that really worked for her.

Princess Diana shopping in Knightsbridge, London, in 1994 and sporting a cropped haircut and tailored outfit paired with loafers. Photo: WireImage

But her style also changed over the course of the decade. The Princess’ divorce from Charles – which took place in 1996 and which will no doubt form a central storyline in this upcoming season – marked a turning point for Diana’s aesthetic. With the help of stylist and friend Anna Harvey, she stripped back her wardrobe and replaced the pastel jumpers and puffy sleeves with beautiful blazers, straight-leg jeans and loafers, and even a new cropped haircut.

I love all her 90s office wear ... It could have been conservative but it wasn’t at all – instead she looked like a hot Ally Mcbeal

Eloise Moran, author, The Lady Di Look Book

Free from any constraints, she looked sleeker and sexier than she ever had before, and courted new designers like Gianni Versace and Jacques Azagury. The latter made her a low-cut Chantilly lace dress for her 36th birthday. “It was her way of saying, ‘I can wear black now, I can do what I want’,” Azagury later said.

Princess Diana at the Metropolitan Museum of Art in John Galliano’s first-ever design for Dior, which was described as “the greatest publicity coup in fashion history”. Photo: Getty Images

From that point on, everything emphasised her shape. Freed from strict royal household rules around how much skin could be shown, she looked entirely A-list in everything from her headline-grabbing silk negligee dress (John Galliano’s first-ever design for Dior, which was described as “the greatest publicity coup in fashion history”) to her post-gym uniform of cycling shorts, sweatshirts and trainers – a combination still copied by influencers like Hailey Bieber today.

Princess Diana, photographed in London after leaving the gym. Her workout clothes have inspired celebrities like Hailey Bieber. Photo: WireImage

“She started to embrace a more American aesthetic at this point,” says Eloise Moran, the author of The Lady Di Look Book. “New York fashion was pushing the minimalist trend and there were rumours Diana might move to Manhattan – she loved America and America loved her, and I think that’s why in the last years of her life she often wore styles that originated over there.”