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Home / Lifestyle

Why Princess Diana's wardrobe was her superpower

By Melissa Twigg
Daily Telegraph UK·
31 Aug, 2022 12:00 AM7 mins to read

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The Princess of Wales always made a statement with her outfits and, 25 years on, her style remains a key part of her legacy. Photo / AP

The Princess of Wales always made a statement with her outfits and, 25 years on, her style remains a key part of her legacy. Photo / AP

When Lady Diana Spencer married Prince Charles on July 29 1981, she claimed she had just "one long dress, one silk shirt and one smart pair of shoes" in her wardrobe. By the time she died, she had become not merely a famous clotheshorse but the most photographed woman in the world and an icon of 20th century glamour.

During her first decade within the palace walls, Diana rarely spoke about the tumultuous life she was leading, the result being that a ravenously curious public turned to analysing her outfits instead. Never a particular fan of fashion before her engagement to Charles, the princess quickly learned that clothes were the best way of expressing her personality and emotions.

1981: Attending a polo game with Sarah Ferguson (before either married a prince). Photo / Getty Images
1981: Attending a polo game with Sarah Ferguson (before either married a prince). Photo / Getty Images

Nobody – least of all the Royal Family – could have predicted the power Diana would one day wield when she arrived on the scene as a shy 19-year-old nursery school assistant, with a wardrobe of floral "accidentally see-through" skirts, sheep-patterned jumpers and yellow dungarees.

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At that point, the world was desperate to turn her into a fairytale princess and Diana was so young that she made this transformation easy.

1981: Princess Diana at the Guildhall in London the day it was announced that she was pregnant with Prince William. Photo / Getty Images
1981: Princess Diana at the Guildhall in London the day it was announced that she was pregnant with Prince William. Photo / Getty Images

"Her [Elizabeth and David Emanuel] wedding gown was the ultimate example of Diana living out the dreams of millions of girls," says the Telegraph's fashion director, Bethan Holt. "All that tulle, and the absurdly long train were everything that comes to mind when we conjure a vision of the perfect princess."

In 1980, Diana (with engagement to Charles imminent) began working with the now late Anna Harvey, a British stylist who would later become an editorial director at Conde Nast. Over the years, Harvey helped the princess with every aspect of her style, whether it was outfits for foreign tours and royal engagements or pieces to wear in her private life.

1982: Princess Diana attending a charity event. Photo / Getty Images
1982: Princess Diana attending a charity event. Photo / Getty Images

At first, the two women played it safe and, conveniently, the princess fantasy chimed with the New Romantic trends of the time: frothy, frilly dresses, ruffled blouses and diaphanous skirts. "There was this veneer of idyllic femininity in all her outfits," says Holt. "Of course we now know that those clothes were a mask for the trouble behind closed doors rather than a way of communicating what was happening and how she really felt."

It was only in March 1983, when Charles and Diana went on their infamous tour of Australia, that Harvey helped Diana show a bolder side. Australia fell in love with the princess and the hourglass white dresses, the colourful skirt suits, the hats and the silk evening gowns were a huge part of why. "If you're shy, clothes can give you confidence and Diana benefited from that – her gowns were her armour," says Holt.

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1983: Diana attends the premiere of Octopussy. Photo / Getty Images
1983: Diana attends the premiere of Octopussy. Photo / Getty Images

Later that year, she wore a slinky one-shoulder beaded dress by Japanese designer Hachi to the Octopussy premiere. "She had begun playing with glamour and becoming much more daring," said Harvey. "The establishment hated [that dress]. It was too revealing; they didn't think it was royal… But she was proud of her figure and how feminine it was – and she wasn't going to be pushed around."

The Shy Di years were over; Dynasty Di had arrived, and the princess turned to designers such as Bruce Oldfield and Catherine Walker in her quest for sleek suits and daring dresses. "It was her way of asserting herself but probably also a way to seek validation from newspapers, magazines and the public when she didn't feel she was getting it from her husband," says Holt.

1986: Princess Diana on an official visit to Japan. Photo / Getty Images
1986: Princess Diana on an official visit to Japan. Photo / Getty Images

By the late 1980s, Diana had stopped abiding by most Buckingham Palace's rules. "As her confidence grew, her outfits became chicer than ever and she developed her own hands-on, not-before-seen brand of princessing," says Eloise Moran, the author of The Lady Di Lookbook. "She declined to wear formal gloves [like other Royals did] because she wanted to appear relatable, with actual skin-to-skin contact when she shook hands."

The people who were dressing her were of course aware of Diana's weight loss. Worried about leaks to the press, the princess closed ranks, ordering dresses from a variety of designers but using the famously discreet Catherine Walker as her sole personal couturier in the later years of her marriage. Over the course of their working relationship, Walker made 1000 of her suits, dresses, and gowns but never spoke publicly about her most famous client.

1986: Princess Diana. Photo / Getty Images
1986: Princess Diana. Photo / Getty Images

It was in the 1990s, though, that Diana's fashion sense truly blossomed. The frills and flounces, the big collars and the shoulder pads of her Sloane Ranger and Dynasty years had been replaced by a cooler, sleeker and altogether more subversive fashion sense. "I became fascinated by Diana when she started mixing high and low trends," says Alessandra Rich, the designer who regularly dresses the Duchess of Cambridge. "It was so unusual then and still looks very modern today. She had the most incredible eye."

As Diana moved into her 30s, she started experimenting: sweatshirts over jeans with a tailored blazer on top and even tracksuit trousers worn with cowboy boots and a cap. "This is an all-time favourite look of mine," says Moran. "It throws all royal conventions out the window and says 'I'll do what I want'."

In 1992, during the death throes of her marriage, Diana was photographed alone at the Taj Mahal – the famous monument to lost love – wearing a Catherine Walker red and purple suit; conveniently, the colours of power. Two years later, on a warm summer evening in 1994, as Charles appeared on TV to confess to Jonathan Dimbleby that he had been having an affair with Camilla, Diana arrived at a Serpentine Gallery party in a Christina Stambolian off-the-shoulder cocktail dress that showed off her fantastic legs. Interestingly, she had bought a far-less revealing Valentino gown but changed her mind at the last minute, and, lo, the "Revenge Dress" was born.

1994: Diana in THAT dress. Photo / Getty Images
1994: Diana in THAT dress. Photo / Getty Images

"That outfit said so much about how she wanted to be perceived as strong and not a weak victim," says Holt. "There were subtler plays with fashion, too – on the day that her separation from Charles was announced in the House of Commons, she wore a Chanel jacket – with its signature CC buttons, a logo she later vowed never to wear again because they were Charles and Camilla's initials."

Post-divorce, Diana stripped back her style and found a uniform of beautiful blazers, tailored trousers or jeans and loafers, and even a new cropped haircut. 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 said.

From that point on, everything she wore emphasised her incredible figure, from a 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 Chelsea Harbour Club uniform of cycling shorts, sweatshirts and trainers – a look that is still copied by Gen-Z models today.

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1995: Diana dons a Versace dress to attend a charity concert in Italy. Photo / Getty Images
1995: Diana dons a Versace dress to attend a charity concert in Italy. Photo / Getty Images

Diana was arguably never more captivating than in her final summer, as she sailed the Mediterranean with Dodi Al Fayed. Her monochrome tank tops and shorts would still look fashionable today, as would those animal print and rainbow one-pieces by Israeli designer Gottex that she wore with matching sarongs.

Most memorable of all, was a turquoise swimming costume she was photographed in as she sat alone on the edge of a diving board. It was August 24, 1997 – seven days before she died – and like so many images of Diana, it is beautiful, but also terribly poignant.

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