Diana, Princess of Wales, remains to this day one of the most fashionable royals of all time.
Though Catherine, Duchess of Cambridge, and Meghan, Duchess of Sussex, have certainly made their mark on royal style, Diana’s place in the fashion history books simply can’t be questioned.
She first stopped the world when she stepped out in her taffeta wedding dress with a cathedral train on the day of her marriage to Prince Charles.
Soon after, she made waves by embracing modern styles and new trends in ways royal ladies never had before.
And who can forget the first time they saw photos of Diana in her breathtaking “revenge dress” at a Vanity Fair party in 1994?
This year marks the 25th anniversary since the ‘People’s Princess’ was suddenly killed in a devastating car crash in Paris on August 31, 1997.
Her legacy of humanitarian work, charity efforts and compassion live on today, and so too does her legacy of royal fashion.
To honour Diana, we are looking back at some of her most incredible style moments, from her first days as a royal, to her final days alive.
Scroll through to see Princess Diana’s most iconic and show-stopping fashion moments through the years.
In 1980, the world learned that Prince Charles was off the market and Lady Diana Spencer was his bride-to-be. Everyone wanted to know about Diana and what she was wearing, though at the time her fashion sense was still quite reserved – as seen in this snap from outside her London flat.
Diana attended her first royal engagement with Prince Charles on March 9, 1981, before their wedding, and set the press ablaze with this risque black dress. The strapless design with a plunging neckline didn’t quite fit royal style protocol and caused some scandal.
On 29 July, 1981, Diana said “I do” and became Princess of Wales wearing this incredible wedding gown, which immediately made royal bridal history. Designed by David and Elizabeth Emmanuel, it featured a 25ft-long train and puff sleeves that dominated bridal styles in the years that followed.
This outfit from Diana’s honeymoon with Prince Charles was a unique choice and set a new ’80s trend. The tweed suit was designed by Bill Pashley and hinted at a love of tailored suits Diana would embrace in the years to come.
In November of 1981, Diana donned this fairytale gown designed by Bellville Sassoon and wowed fashion lovers everywhere. Not only did her dress make headlines, the very next day she announced she was pregnant with her first child, Prince William.
When Diana stepped out onto the dance floor in Washington with film star John Travolta in 1985, no one could take their eyes off her. The princess was dressed in a Victor Edelstein midnight blue velvet gown that went on to sell for over $497,000 at an auction in 2019.
Ever the fashion forward-thinker, Diana chose to wear an heirloom royal necklace as a headband during a 1985 engagement in Melbourne, Australia. She wore the art deco emerald choker, gifted to her by the Queen, around her forehead and paired it with a teal evening gown designed by her wedding dressmakers, David and Elizabeth Emanuel.
You could be forgiven for mistaking the princess for a Hollywood movie star in this chiffon ensemble she wore to the Cannes Film Fetsival in 1987. The dress and matching chiffon stole were designed by Catherine Walker.
The revenge dress. That’s what the world called the little black Christina Stambolian frock Diana wore to a Vanity Fair party on November 20, 1994. She wore it on the very evening that Prince Charles made his notorious adultery admission on television, but it was Diana’s style that made headlines.
Who could forget Diana’s most stylish casual combo: a sweater and bike shorts. This particular ensemble has gone down in history as one of her best, the princess pairing a Virgin Atlantic sweatshirt with orange shorts as she left Chelsea Harbour Club in London in November, 1995.
Back at another Vanity Fair party in 1995, Diana wowed again in this plunging cocktail dress deigned by Catherine Walker. By this time, her divorce from Prince Charles was underway and Diana was starting to don more daring styles as she moved away from royal style restrictions.
It may not have been her most upscale look, but Diana made history in 1997 when she donned protective body armour and a visor to cross a landmine minefield being cleared in Angola.
In June of 1997, less than two months before she died, Diana attended a performance of ‘Swan Lake’ by the English National Ballet wearing this frock by French designer, Jacques Azagury. Its short hemline and cleavage-baring neckline were a stark contrast to her early royal fashion choices and spoke of Diana’s new freedom as a divorced former royal.
Diana went all out for her 36th Birthday on July 1, 1997 donning this incredible black gown designed by Jacques Azagury for an appearance at the Tate Gallery in London. It was one of the last formal events she would attend before her tragic death.
In the summer before her death, Diana was seen wearing a colourful swimsuit and cover-up as she holidayed in St Tropez, France. Looking relaxed and sunkissed, photos of the princess dressed so casually made headlines as she settled into her new life outside of the monarchy.
It seems only fitting that one of the last photos ever taken of Diana, Princess of Wales, shows her dressed down in a plain white button down and jeans. Seen here in Bosnia – Herzegovina on August 9, 1997, Diana proved her style legacy wasn’t just about expensive gowns and lavish frocks. In fact, it was her more approachable and ‘normal’ fashion moments that helped make her the beloved ‘People’s Princess’ we all remember today.
