Princess Diana's fashion legacy: looking back at the royal's memorable style moments

From a fairy-tale wedding gown to the ultimate 'revenge dress', the Princess of Wales was the original fashion influencer

Diana, Princess of Wales and Prince Charles on their wedding day. Getty Images

Princess Diana would have celebrated her 60th birthday on Thursday, a day that will be commemorated by the unveiling of a statue of the late Princess of Wales in the gardens of Kensington Palace by her sons, the Dukes of Cambridge and Sussex.

What had begun as a fairy-tale story about a princess aged 19, but ended in tragedy in Paris in August 1997, is highlighted by a dazzling display of her wedding dress in the palace's Orangery.

A wedding dress to remember

Princess Diana's wedding dress by David and Elizabeth Emanuel at the Royal Style in the Making exhibition at Kensington Palace. Courtesy Matthew Storey

It is the first time the two dukes have permitted their mother’s wedding dress to be displayed. The design by David and Elizabeth Emanuel captivated the world. Matthew Storey, curator of Historic Royal Palaces and the exhibition Royal Style in the Making, tells The National that he was bowled over when he saw the dress in person for the first time.

“Like the 750 million, I tuned in to watch the wedding, but it is only up close you realise how beautifully made it was and how it comes alive in the details and sparkle,” he says. The Emanuels wanted and delivered “a fairy-tale princess dress”.

Thousands of brides copied the look for their own wedding gowns, starting a feverish appreciation of Diana’s sartorial choices long before it-girls and fashion influencers took over social media feeds. During the 1980s and 1990s, Princess Diana was the most photographed woman in the world, each of her style choices carefully documented by the local and international press.

Now a younger generation is introduced to her through Emma Corrin's portrayal of Diana in The Crown.

A designer's dream

Designer David Sassoon, of Bellville Sassoon, who created the princess’s “going-away” outfit (that is also part of the Royal Style in the Making exhibition) and her wedding trousseau recalls a splashy floral printed dress he designed for Diana, which she dubbed the caring dress.

“Children relate to very bright colours, and she would often pick up a child and they would stroke the dress,” Sassoon tells The National, “but she was told by the newspapers not to wear it any more as she wore it so often.”

Princess Diana had a soft spot for children and was often photographed interacting with them. Getty Images

New dresses, after all, ensured front-page photographs.

Sassoon, now 88, and the late French-born designer Catherine Walker were a couple of Diana’s most enduring fashion relationships. “I was lucky, she was very charismatic and a great joy to work with because she had a great sense of humour,” says Sassoon. However, every fashion designer wanted to dress this tall, slim, beautiful woman, including Jasper Conran, Rifat Ozbek, Gina Fratini and Victor Edelstein – and she obliged.

Princess Diana had star power and appealed madly to young women. She also dared to buck the old established royal rule that making a fashion statement is mildly suspect and should be avoided wherever possible. She eschewed gloves, wore diamond necklaces as headbands and even sported a tuxedo.

Princess Diana at the White House in 1990, with the first lady at the time, Barbara Bush. AFP

“In terms of fashion, she could just wear it, as she had a tall frame, good wide shoulders, a narrow waist and hips, a size 10, and she looked great in most things,” specialist auctioneer Kerry Taylor, who has auctioned 32 of Diana’s dresses and ensembles over the past 20 years, tells The National.

The people's princess

“The interest in the princess is enduring,” Taylor says, referring to the buzz that surrounds each dress that comes up for sale. “We had a beautiful white moss crepe dress by the Emanuels that the princess wore on a visit to the Gulf, which created a lot of excitement with people from the Middle East bidding on it. The more the pieces she wore have been photographed, and she wore them on a few occasions, it helps raise the price. That dress sold in 2018 for £130,000 ($180,000).”

Catherine Walker's sequined gown for Princess Diana's state visit to Austria, which sold at auction by Kerry Taylor for £75,000

Bidders from countries that the princess visited “would like to have a little bit of Diana to take back”, says Taylor, who also sold the Emanuels’ strapless black taffeta ball gown Diana wore to Goldsmiths’ Hall soon after her engagement announcement.

It had caused a huge stir in the press for its low neckline; “Di takes the plunge” read many a headline. “She must have been so embarrassed,” says Taylor.

Learning the ropes

The voluminous romantic gown, however, was typical of the fashions in the early 1980s; along with the piecrust frill necklines and pleated skirts, it was rather conservative. The eveningwear, however, got ever more flamboyant until 1985, when Princess Diana swept into Washington, DC with such a volume of cargo that the British tabloids dubbed her “Dynasty Di”. The criticism stung.

Diana was a romantically minded woman, brought up in the tradition of obedience and deference to the Crown. “She was only 19 when she got engaged and she had not had clothes made for her before,” says Sassoon, and so it was a bit of a learning process. “It was an exciting experience [for her], like being a child in a sweetie shop.”

Bellville Sassoon's sketch for Princess Diana's 'caring dress'

Diana helped put British fashion on the map with guidance in the early days from Anna Harvey, senior fashion editor at British Vogue. While she enjoyed fashion, as Said Cyrus, Walker’s widower who worked alongside his designer wife, points out, "people forget that the princess was doing a job as an ambassador, and we were giving her the tools to do that job".

She was minimally involved in the design process: “The briefs got shorter and shorter. I would do the drawings for the presentation to the princess who would write notes on the back,” Cyrus tells The National.

Lydia Slater, editor of British Harper’s Bazaar, describes Princess Diana as “absolutely brilliant at communicating with her clothes”, noting the famous “revenge dress”, with its daring off-the-shoulder silhouette that she wore to an event on the very night Charles, the Prince of Wales, confessed infidelity on national television. It was, says Slater, “a statement of defiance”.

Style evolution

Princess Diana’s clothes were a semaphore for the changing patterns of her life. After the Dynasty Di barb in the late 1980s, she developed a sleeker, low-key style that reflected her emergence as a confident woman. Walker helped her evolve that graceful, elegant look that better suited the princess’s needs as she went about her charitable and humanitarian work.

Founding Father Sheikh Zayed with Prince Charles and Princess Diana in Abu Dhabi in 1989. Courtesy Zaki Nusseibeh / Akkasah Center for Photography

The designer developed a refined style of tailoring that suited Diana well: lean suits and coats with a strong shoulder-line and no waistline, which looked impeccable but never uptight. She also always chose a great colour that would be spotted in crowds.

“She had massive blue eyes and picked things to emphasise them,” says Taylor. And, says Storey, “she loved it when the press made a fuss about a garment of hers”.

After her divorce, Diana shrugged off the stilted dress codes and wore what she liked, so her dresses became a bit more alluring.

Britain's Diana, Princess of Wales at the opening of Paul McCartney's oratorio "Liverpool" in 1992. AFP Photo

She started wearing Chanel, Dior, figure-hugging Versace, as well as sticking with Catherine Walker. She embraced contemporary gym culture, mixed designer and high-street fashion, and wore accessories such as Tod’s Gomminos, and Dior and Ferragamo handbags that were subsequently renamed in her honour.

The current piecrust collar trend, the slogan sweatshirts, the tailored blazers are all throwbacks to looks that Lady Diana popularised and that are now endlessly mined on social media. She was a style icon for one generation and now, potentially, for another.

Royal Style in the Making is on until January 2, 2022 at Kensington Palace, London; hrp.org.uk