The Crown's New Season of Has All of Diana's Most Famous (and Infamous) Dresses

It is one of the most enduring images of the last century, Princess Diana arriving at the Serpentine Gallery, in London’s Hyde Park, on June 29, 1994, in a black dress. It was the night that the future King Charles III memorably admitted to having an affair with the current Queen Consort, Camilla. She still managed to push her husband off the next day's front pages, however, with a now-infamous gown. Wearing a black silk crepe Christina Stambolian creation, along with her favorite sapphire, pearl, and diamond choker, her matching engagement ring, and scarlet-red nails, Diana made a statement to the world that she was not going to shrink away, despite the state of her marriage.

The American press dubbed the showstopper the "Revenge Dress," while Britain’s Telegraph newspaper described it as the "piece de resistance," and claimed it was "possibly the most strategic dress ever worn by a woman in modern times." However, it was only a spur-of-the-moment decision that led Diana to wear the dress, which she had bought three years earlier after having lunch with her brother Earl Spencer, at her favorite restaurant, San Lorenzo.

Diana had actually been planning to wear a Valentino number that night. However, when her outfit leaked to the press, she was furious. "She went to Valentino to get a dress for that particular date she had at the Serpentine," Christina Stambolian told me in an interview for my book, Diana: A Life in Dresses. "Then Valentino rang all the newspapers saying, 'She’s coming out with my dress tomorrow.' She heard that, and Diana said, 'There’s no way I’m going to do him a favor. I’m going to wear another dress.'"

Instead, Diana and butler Paul Burrell chose a daring, low-cut black dress. "I was thrilled to see Diana wear it on that night of all nights. She chose not to play the scene like Odette, innocent in white," said Stambolian referring to one of Diana’s favorite ballets, Swan Lake. "She was clearly angry. She played it like Odile in black. She wore bright red nail enamel, which we had never seen her do before. She was saying, 'Let’s be wicked tonight.'"

This week, the dress is having a second life on the silver screen with the release of new episodes of The Crown. For the show, assistant costume designer Sidonie Roberts, who won an Emmy for Outstanding Period Costumes in season three of the Netflix hit, recreated the dress. It's one of the fashion highlights of the highly anticipated—and controversial—fifth season. The scene is a marvelous trip down memory lane, not only for recalling the extraordinary love triangle between Charles, Diana, and Camilla but for recreating the fashions of the era, when the Princess was one of the most photographed women in the world.

"We can't overestimate its impact," Roberts says of the Revenge Dress. "In the Revenge Dress, not only do we have the birth of a new woman, we have the birth of an icon for women all over the world. It was a deeply empowering moment."

In the latest series, in which Elizabeth Debicki takes over from Emma Corrin as Diana, we see the Princess of Wales stepping into her own as a sex symbol. As she finalizes her separation from Prince Charles, she emerges with a whole new sense of self—and her wardrobe reflects that evolution. Gone is the Old Diana, with her high collars, frilly dresses, and preppie loafers. The new Princess Di is a sizzling style icon, as sleek, elegant, and sophisticated as a supermodel.

According to costume designer Amy Roberts, the team wanted to "catch the spirit of Diana" rather than replicate her famous wardrobe. But they have gone to great pains to recreate some of Diana’s outfits which are seared into the public consciousness, such as her Emanuel wedding gown, worn by Corrin in the last series of The Crown, and the Revenge Dress, worn by Debicki, in episode five of this season.

"We know everyone is waiting for those moments and try to do them justice by steering as close to the reality as possible," added Roberts. "There is an extensive amount of research involved."

In the first episode of the new series, Diana, played by Debicki, is seen standing majestically on the deck of a yacht with Prince Charles, played by Dominic West, in a patterned dress, reminiscent of the dress that fashion designer David Sassoon dubbed her "Caring Dress," as it was designed in primary colors to appeal to schoolchildren. She's still in her Old Diana phase, favoring styles that adhere to royal protocol and emphasize her role as a mother and wife.

In a later scene, Debicki is shown dancing at a ball in Scotland, wearing a white ballgown with an orange sash, similar to the gown that Diana wore to one of the Royal Caledonian balls. Later in the series, we see her dropping off Prince William at Eton in a black dress and royal blue blazer in 1995. Afterward, she's shown being interviewed by Panorama reporter Martin Bashir later that year in a black trouser suit and white top. The succession of these outfits speaks to her state of mind: Diana steps into her power wearing, of course, a sharp black suit.

We see The Crown's final evolution of Diana, like a butterfly fully emerging from its chrysalis, on a visit to the Swan Lake ballet at London’s Royal Albert Hall in 1997. She wears an ice blue beaded dress, which appears to be based on a Catherine Walker dress that Diana wore to a party two years earlier, rather than the actual Jacques Azagury number Diana wore in real life.

Diana: A Life in Dresses From Debutante to Style Icon is published by ACC Art books and is available for $40 on Amazon.