Princess Diana's Enduring Style Legacy

by Violet Conroy on 13 November 2020

The influence of the people's princess can be felt in today's trends for athleisure, streetwear and preppy modes of dressing. Ahead of the release of Season 4 of The Crown, we trace Diana's evolution from Sloane to style icon.

The influence of the people's princess can be felt in today's trends for athleisure, streetwear and preppy modes of dressing. Ahead of the release of Season 4 of The Crown, we trace Diana's evolution from Sloane to style icon.

In the trailer for the highly anticipated fourth season of The Crown, our first glimpse of Princess Diana is from behind, as she steps onto a street lined with paparazzi. She is instantly recognisable with her short, feathery blonde hairdo emblematic of the Sloane Ranger years in which the princess favoured green barbours, cashmere tank tops, dainty cardigans, tweed jackets and wellington boots.

The way in which Diana chose to present herself publicly through dress was of the utmost importance. As the heir apparent to the British throne, she was one of the most photographed women in the world, globally scrutinised by the press up until her untimely death in a car crash in 1997. Eschewing traditional royal dress codes, Diana refused to wear gloves while meeting AIDS patients in the 1980s despite rumours that the disease could be transferred through skin-to-skin contact. She showed off her shoulders in form-fitting midi dresses, painted her fingernails in bright colours and wore black outside of funerary occasions - all decisions that broke royal protocol. ‘Her clothing tells the story of her coming of age in a way that speaks for itself,’ Emma Corrin, the 24-year-old actress playing Diana in The Crown, told Elle.

Emma Corrin on the cover of the October 2020 edition of British Vogue. Photo by Charlotte Wales

As Diana’s marriage to Prince Charles began to disintegrate following the couple’s separation in 1992, Diana’s style underwent a radical transformation which was to become more glamour than galoshes. The upcoming season of The Crown covers the time period between 1977 to 1990, so fans of Diana’s more daring looks will have to wait for Season 5. Alternatively, Kristen Stewart is set to play Diana in Spencer, a film currently in pre-production that centres on the weekend in which the princess decided her marriage to Prince Charles was no longer working.

For now, the definitive source for the princess’ ‘sassiest post-divorce looks’ is the Instagram account Lady Di Revenge Looks. Images of Diana in casual off-duty looks are most resonant: Diana in athleisure, wearing sunglasses, colourful cycling shorts and baggy Harvard sweatshirts, Diana with her trousers tucked into cowboy boots, an oversized blazer and cap thrown on or Diana in the notorious black ‘revenge’ dress, worn on the same evening that Prince Charles publicly confessed to his adulterous relationship with Camilla Parker Bowles. ‘Diana’s style was utterly anti-establishment. She was keen to experiment with wearing sportswear styles in public (a huge no-no for the royal family) as well as adrogynous looks. She took a normcore approach to royal dressing, which is cool,’ said the founder of Lady Di Revenge Looks, Eloise Moran, over email.

‘Normcore,’ a portmanteau of the words normal and hardcore, is an ironic term popularised by trend forecasting group K-HOLE in 2013 which pertains to an atittude of ‘acting basic,’ although the term has since evolved to encompass a casual way of everyday, unisex dressing in items like T-shirts, jeans, and sweatshirts, all of which the princess favoured.

‘Normcore’ is not the only 21st century internet aesthetic that the princess seems to neatly slot into. Talking of the current vogue for wellington boots, emblematic of the wider nostalgic ‘cottagecare’ trend, Lauren Cochrane, senior fashion writer for The Guardian wrote, ‘A picture of a young Princess Diana in the countryside wearing Hunters in 1981 has become a style reference for a new generation.’ Diana’s uncanny ability to remain relevant in fashion’s contemporary consciousness, aside from fleeting internet trends, is also down to a mix of continued celebrity and fashion establishment endorsement.

Prince Charles and Princess Diana in 1981. Photograph: Scotland/Rex/Shutterstock

In 2019, Hailey Bieber modelled in a shoot for Vogue Paris mimicking off-duty paparazzi shots of the princess, while Rihanna, one of the most influential women in the world, told Glamour in 2013, ‘You know who is the best who ever did it? Princess Diana… She was gangsta with her clothes.’ The contemporary trend for athleisure, exemplified in paparazzi images of celebrities like Emily Ratajkowski and the Kardashians clad in lycra cycling shorts, mirror those taken of Diana in the 90s, although Kim and Kendall tend to favour stilettos over sneakers.

Fashion-wise, Diana’s influence can be felt in the spheres of streetwear and a more bourgeois type of dress, pointing to both her universality and versatility. Rowing Blazers, an American preppy revival brand, recently recreated two memorable intarsia sweaters Diana had previously worn, with one sporting a tongue-in-cheek phrase: ‘I’M A LUXURY’ is printed on the front of the sweater, ‘FEW CAN AFFORD’ on the back. ‘It feels like the kind of thing Demna Gvasalia might design if he’d gone to Eton and became an 80s Sloane Ranger - but it also couldn’t be more 2020 if it tried,’ says features editor of Buffalo Zine and contributing writer for, Liam Hess. Virgil Abloh, widely known as the ‘king’ of streetwear, paid homage to Diana in his Spring/Summer 2018 Off-White collection after trawling through archival 90s paparazzi pictures of the princess. Palace, a cult London-based skateboarding label favoured by teenage boys and high-profile celebrities like Drake and Jonah Hill, printed a 1982 image of Diana onto T-shirts in 2017, despite receiving a cease and desist order from none other than the royal family.

Sam McKnight, the mastermind behind Diana’s influential short hairstyle, spoke to SHOWstudio about the princess’ 1991 Patrick Demarchelier Vogue cover. ‘I don’t think she ever found them (photoshoots) particularly easy. It wasn’t her comfort zone to be sitting there in a studio with lights and six people staring at you, having her hair and makeup done,’ said McKnight. What would Diana make of the enormous style legacy she left behind? ‘Everyone who worked with her recalls that she knew what she liked and was very active in her own image-making,’ said the curator of 2017 exhibition Diana: Her Fashion Story in The Guardian. As a public-facing woman of few words, Diana's clothes and kohl-ringed doe eyes betrayed a wealth of emotional intelligence, playfulness and nonconformity that has celebrities and designers rapt today, over 20 years after her death.

Princess Diana on the cover of Vogue in 1991. Photo by Patrick Demarchelier



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26 September 2014
Sam McKnight talks to Nick Knight about working with Princess Diana on a 1991 Vogue shoot, as well as some of her most iconic hair looks.
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