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Princess Diana: Her Most Iconic Looks

As the most photographed woman in the world, Princess Diana had to ensure that she was putting her best fashion foot forward at all times – and she rarely failed. 

A lover of designers such as Versace, Catherine Walker, Chanel and Bruce Oldfield, Diana’s unique sense of style captured the attention of people around the world and challenged everything that we knew about the royal wardrobe. 

Diana’s signature look continued to develop and shift throughout her time within the public eye, as she adapted flawlessly to changing trends and created brand new ones, too. Widely considered one of the world’s best dressed women during and after her marriage to the Prince of Wales, all eyes were on Diana wherever she went – and she certainly always rose to the occasion. 

Here, we take a look back at some of Princess Diana’s most iconic looks, including the controversial dress she chose to wear to her first royal engagement and her now-infamous ‘revenge dress’. 

The Yellow Dungarees

Diana had a penchant for pulling off a casual look in a way that few of her fellow royals ever had before her, perhaps inspiring the modern smart-casual style adopted by the Duchess of Cambridge to this day. 

Here she is at a polo match in 1981, beautifully matching a pair of summery yellow dungarees with a floral shirt and pink espadrilles.

Her Engagement Announcement Look

It may surprise you to hear that the iconic blue skirt and blouse that Diana wore following the announcement of her engagement to Prince Charles were picked out at a department store. 

Diana told her biographer Andrew Morton that she had no clothes prepared for her new role as a working royal right up until her engagement, leaving herself and her mother raiding the rails in London’s Harrods to pick out a whole new wardrobe at the very last minute, including this famous two-piece. 

Her Controversial Black Taffeta Gown

On the evening of her first official royal engagement, Diana opted for this chic strapless black gown designed by The Emmanuels, who would go on to design her wedding dress. 

Whilst undeniably beautiful, the choice proved controversial – both the colour and silhouette of the gown were a far-cry from the dresses that women within the royal family had opted for in the past. It’s been said in the past that the Prince of Wales himself was less than impressed by the gown…

Her Honeymoon Look

As Princess Diana and her new husband made their way to Hampshire’s Eastleigh Airport to jet off on their honeymoon, she decided on a glamorous floral wrap dress by Donald Campbell. 

Her First Royal Tour Wardrobe

As the newlywed Prince and Princess of Wales embarked on their first official royal tour of Australia, Diana commanded attention in this beautiful pink polka dot dress and hat by Donald Campbell.

The look was one of several famous outfits from Diana’s wardrobe that were recreated for Emma Corrin in season 4 of The Crown. 

The Pink Gingham Trousers

Princess Diana (1961 – 1997) during a visit to Perth, Australia, March 1983. She is wearing a dress by Donald Campbell and a hat by John Boyd. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)

Pictured outside her country home in Highgrove in 1986, Diana opted for a pair of ankle-grazing trousers in a pink gingham print. While many of Diana’s looks are reminiscent of the time in which she wore them, this particular outfit would likely look just as on-trend in 2021. 

The Baby Blue Cannes Dress

Diana appeared to be channeling a Greek goddess as she attended the Cannes Film Festival back in 1987, stepping out in this strapless gown by Catherine Walker. 

Her Thailand Tour Wardrobe

All eyes were on Diana during the royal couple’s many international tours, their trip to Thailand in 1988 being no different. 

Always armed with an exceptionally stylish tour wardrobe, Diana was once again dressed to impress. Here she is in a stylish knee-length skirt and patterned blouse combo during a brief sojourn in Bangkok. 

The Red & Black Houndstooth Suit

Not the first of Diana’s stylish Houndstooth suits, nor her last – however, this red and black combination by Moschino is perhaps her most iconic. Diana wore the blazer in particular on several occasions, most famously to greet a young Prince William and Prince Harry as they joined their parents on an official visit to Canada in 1991. 

Her Look At The Taj Mahal

During a visit to the Taj Mahal in 1992, the Princess paired a vibrant purple skirt with a bright red jacket.

Later that day, Diana was photographed sitting alone outside the romantic world-famous landmark, with the world’s media using the sombre photos to speculate on her unhappy marriage to Prince Charles and whether her increased solo appearances were a sign that an official split was imminent. 

The Revenge Dress

Following her split from Prince Charles, Diana began dressing a little more daringly, holding firmly onto her reputation as one of the world’s best dressed women. 

Perhaps her most iconic look, Diana marked the airing of a documentary in which Prince Charles admitted he had been unfaithful to Diana by appearing at a charity event in this chic Valentino gown, famously dubbed ‘the revenge dress’ ever since. 

Her Athletic Street Style Looks

She may have been ‘the People’s Princess’, but when it came to street style, Diana was queen. 

Throughout the early 90s, Diana showcased a variety of exceptionally cool athleisure and sports luxe combinations, most famously teaming oversized sweaters with cycling shorts and chunky sneakers – a trend that continues even now, favoured by 21st century stars such as Bella Hadid and Hailey Bieber

The Versace Mini Dress

Diana had always been an unofficial poster girl for Versace, representing the brand on several occasions. 

This white mini dress by the label was a perfect choice for Diana, who wore it to a charity concert in Italy in 1995. 

Vibrant Bikini Look

In one of the final photographs of Diana during her ill-fated trip to the South of France, the princess looked characteristically vibrant as she relaxed on a yacht.

Her life would be tragically cut short just hours later due to a high-speed car accident. 

However, her legacy has lived on in the twenty years since, as Diana is remembered not just as a royal, a philanthropist and the mother to the future king, but as a true and timeless style icon.

READ MORE: The Inside Story Behind Princess Diana’s Infamous ‘Revenge Dress’