Princess Diana fashion: Charting her style evolution from from Sloane Ranger to fashion renegade

More than 20 years after her death, Princess Diana’s legacy remains a global obsession. From the Virgin Atlantic jumper she wore to the gym, or the “Black Sheep” crewneck that recently went back on sale, to the velvet gown she wore to dance with John Travolta at the White House, each outfit is as memorable as the moment in which she wore it.

Hers was a wardrobe to suit all tastes, from offbeat mods to strait-laced sloanes, depending on the decade. And while much of it was exemplary of the era (is there anything more 1980s than the leg-of-mutton sleeves and 25-foot train of her Emanuel taffeta wedding gown?), the Diana aesthetic has endured the ages. Today, brands continue to take cues from key looks in the Princess of Wales’ wardrobe, like her peter pan collars and polka dot tea dresses.

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With the world commemorating what would have been her 60th birthday this July, Diana’s style has once again returned to the forefront of fashion discussion. In fact, it has been a topic of interest since last November, when the fourth series of The Crown debuted on Netflix, and saw Emma Corrin playing the late Princess. The series’ costume designer Amy Roberts stays true to Diana’s wardrobe, recreating her looks for the historical drama and illustrating how her style evolved over the years. And what an evolution it was.

Diana was not always the fashion maven we think of her as today. According to fashion historian Eleri Lynn, who curated the 2017 “Diana: Her Fashion Story” exhibition at Kensington Palace, Diana only owned three items of clothing when she got engaged to Prince Charles in 1981: a long dress, a smart shirt, and a pair of smart shoes. “The rest, she shared with flatmates”. However, things swiftly changed as Diana made the transition from low-key aristocrat to bona-fide Princess in a matter of months.

Just as Diana’s life was changing dramatically, so was the media, and this meant an image overhaul. “With rolling news, tabloid journalism, and the dawn of the digital age, Diana had to quickly learn the rules of royal dressing, and so the effect of Diana’s wardrobe on wider public trends was much more immediate than ever before,” said Lynn. “In this new media age the Princess was active in the creation of her own image, and she used fashion to do this. She chose her clothing carefully, almost as a tool, to help her to her job as patron of the arts, diplomat, and humanitarian.”

Meanwhile, in a recent column, ex-Vogue editor Alexandra Shulman credited much of Diana’s style to journalist Anna Harvey, who helped the princess reinvent herself as a fashion icon.

So how did Diana make the unlikely shift from stereotypical sloane ranger to one of fashion’s most revered figures?

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When Diana was first linked to Prince Charles, she was far from the fashion legend she is remembered as today. With pie-crust collars, ill-fitting blouses, tartan smocks, and calf-length hemlines, Diana’s wardrobe resembled that of a typical upper class teenager in the late 1970s, an aesthetic that came to be known as the  “Sloane Ranger” thanks to journalists Peter York and Ann Barr.

While some of her outfits would still pass as fashionable today - plaid skirts and knitted cardis are very autumn/winter 2019 - they were out of touch with the avant-garde looks of the time. Because while the 1980s saw the birth of fishnets and fluoro, Diana stayed true to her sloaney sartorial guns right up until her engagement to Charles.

It was around this time that she met Anna Harvey, the late fashion stylist who worked as deputy editor of British Vogue. "I was shaking like a leaf,” Harvey recalled of their first meeting in an article for Vogue. “But I took one look at her and thought, this isn't going to be too difficult after all. She was about 5ft 10in and completely in proportion. Her eyes lit up when she saw all the racks – I don't think she had any idea how many lovely things there were out there – and her enthusiasm was contagious."

Harvey had a seismic influence on Diana’s wardrobe, easing her out of cumbersome tweeds and heavy knits and introducing her to some of the staple looks that people would come to associate with the late Princess.

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Diana had a thing for polka dots in the 1980s, and was often seen sporting the pattern at high-profile royal events. There was the red and white wrap dress she wore on her 1986 tour to Japan with Prince Charles, the monochrome frock she wore to the Derby Horse Race in later that year, and the unforgettable sky blue pleated dress she paired with white kitten heels at Victoria station in 1989.

It was also around this time that Diana’s penchant for peter pan collars began, a trend that has gathered pace this season. There was the white frilly one she wore on a visit to the National Orthopaedic Hospital in 1984, the abstract pointy one that toppers her crimson cardigan during a 1983 tour of Canada, and the somewhat Shakespearean one she wore underneath a burgundy velvet jacket earlier that year in London.

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Diana’s collection of gowns is unforgettable, but there is a notable distinction between ones she wore in the earlier years of her marriage to Charles compared to the latter years (more on which later).

In the beginning, Diana favoured statement gowns that packed a punch on all fronts, from colour and texture to neck and hemline. There was the canary yellow taffeta number she wore to Sadlers Wells in 1983 (very Beauty and the Beast), the ruched fuchsia velvet gown she wore to a charity gala in Palm Beach, Florida 1985, and then of course, there was the “Travolta dress”.

In November 1985, Diana attended a gala dinner at the White House, where she famously danced with the actor John Travolta. For the occasion, the Princess wore an off-the-shoulder midnight blue velvet gown designed by Victor Edelstein. It was a perfect regal look, one that captured both Diana’s regal status and her sartorial subversiveness.

Shortly before her death, Diana requested that the dress be sold in a charity auction. It was bought by a Florida-based businesswoman, Maureen Dunkel, in June 1997 for £100,000. However, it is now owned by Historic Royal Palaces, a charity that looks after royal clothing and artifacts.

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Just as Diana knew how to don her glad rags, she also knew a thing or two about tailoring. While the Princess wore suits throughout her life, it wasn’t until the early 1990s that she found her feet in the trend. Take the blue skirt suit she wore to announce her engagement to Prince Charles. With its calf-grazing hemline and small waist belt, the look was certainly strong, but it was also of its time.

This cannot be said of Diana’s later tailoring choices. Fast forward a decade, and the Princess had upgraded her tailoring collection to feature more double-breasted andryogynous styles that wouldn’t go amiss in a high street store today. Memorable looks include the pink and purple-trimmed skirt suit she wore to Ascot in 1990, the blue and white buttoned suit she wore on tour in Egypt in 1992, and the pinstripe grey suit she paired with pearls and thick black tights for a lunch in Chelsea in 1995.

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Towards the end of Diana’s marriage to Prince Charles, she stepped things up a notch, sartorially speaking. Her gowns had always packed a punch, but by the early-to-mid 1990s (the couple split in 1991 and divorced in 1996), Diana was regularly seen in showstopping frocks.

There was the scarlet off-the-shoulder gown she wore to the Just Like a Woman premiere in 1992 and the long-sleeved aquamarine sequin gown she wore to a charity ball in 1990. The sheer glamour of the latter was accentuated by the Princess’s matching satin shoes and clutch bag.

And then there was the “revenge dress”. Perhaps her most famous look of all time, the black silk Christina Stambolian gown was worn by Diana to the Serpentine Gallery summer party in 1994 on the same night Prince Charles admitted to having an affair with Ms Parker-Bowles. Triumphant as ever, Diana emerged in the form-fitting, off-shoulder gown, which she paired with black sheer tights and stilettos.

According to the 2013 Channel 4 documentary, Princess Diana’s Dresses: The Auction, the Princess had originally planned to wear a more modest Valentino gown that evening, deeming the Strambolian gown “too daring”. But she reportedly changed her mind when the Italian fashion house sent out a press release announcing her intention to wear their dress. "She wanted to look a million dollars," recalled Harvey in the documentary. "And she did."

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When Diana wasn’t busy with her philanthropic work, she was being a mother to her two sons: Princes William and Harry. But even in these casual moments, where practicality trumped aesthetic, her style never faltered, least of all while on family holidays.

Take the leopard swimsuit she was photographed wearing while jet skiing with Prince Harry in Saint Tropez in 1997, or the low-back sky blue one she wore in a now-infamous photo of her sitting on the end of a diving board while on holiday with her boyfriend, Dodi Al Fayed, in Portofino that same year.

Beyond statement swimwear, another look Diana favoured while holidaying with her children was the oversized T-shirt. There are several memorable photos of the princess standing aboard a yacht in the West Indies in 1995 wearing nothing but a pale pink Tee and a baseball cap. Cargo pants and tank tops were a favoured look, too, and often came in neutral hues, like white and beige.

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Interestingly, some of Diana’s most referenced looks today are some of the most laid-back. Like her gym wear. For most people, a trip to the gym is a laborious task, one that requires lots of layers and lycra. But for Diana, it was yet another chance to showcase her inimitable style.

And she did so with aplomb. Usually, Diana’s gym ensembles would comprise a pair of tight-fitting cycling shorts (remember when those surged in 2017?), an oversized sweatshirt, thick white socks, and chunky trainers. It’s a look that has been so memorialised, it was the inspiration for a recent Vogue Paris shoot fronted by Hailey Bieber.

But Diana’s gym wear had symbolic power, too. One jumper that she frequently wore to work out was a navy blue Virgin Atlantic sweatshirt given to her by Sir Richard Branson. Frustrated with the attention she received from the press, Diana wore the jumper repeatedly in the hope of discouraging paparazzi from photographing her, given that every photo would look the same.

Diana gave the famous jumper to her personal trainer, Jenni Rivett, shortly before her death. It was sold in an auction in 2019 to an anonymous bidder for £42,700.