Princess Diana was not only part of the fashion world's conversation for most of her public life, from her wedding to Prince Charles on July 29, 1981, until her death on August 31, 1997, but despite being the fashion world's buzz leader, she attended the Met Gala attended only once, on December 9, 1996. (Anna Wintour had only chaired the event the year before, in 1995, but she was replaced by the same magazine editor, Liz Tilberis, who did not chair the 1996 event.) Since its formation in 1948, the Met had always been an exclusive and hot ticket, but the "First of May Monday" had not yet reached the peak of its fervor)

On December 9, 1996, Diana passed away, just less than three months after her divorce from Prince Charles was finalized on August 28. Fashion designer Christian Dior, who was a close friend of Diana's, renamed his 1994 handbag "Chou-Chou" the "Princess" in honor of her. Not surprisingly, Diana carried Lady Dior at the MET, and had done so often since first encountering the style in 1995.

At Diana's one and only Met, her star power was intoxicating. She arrived at the Metropolitan Museum of Art in the arms of Tilberis, who was co-chairing the gala that evening. Tilberis succeeded Winter as editor-in-chief of British Vogue in 1987 and became editor-in-chief of Harper's Bazaar in 1992. Princess Diana and Tilberis became friends through a "working relationship and subsequent friendship" during Princess Diana's tenure at British Vogue, and in 1995 Princess Diana made a special visit to New York to present Tilberis with the Council of Fashion Designers of America (CFDA) Award. Tilberis was a member of the Tilberis family for many years. According to Newsweek, Tilberis invited Diana to the Met in 1996 and became "a powerful ally of Princess Diana during her separation from Prince Charles. When Tilberis was battling cancer, Diana often called and wrote to her to offer words of encouragement and comfort, never knowing, of course, that her life would be cut short two years before Tilberis' death.

Because of her relationship with both Tilberis and Dior, the timing was right for Diana to make her Met debut. Vogue magazine wrote, "The royalty appeared in the most un-royal attire and understated manner ever." A Dior slip dress by John Galliano with a lace negligee and matching dressing gown-style robe was a world away from the Diana who once charmed the world in a sheep's jumper, and the newly divorced Diana was released from her Kensington Palace ceremonies, It showed that she was enjoying a new phase in her life," Vogue continues. Royal biographer Katie Nicole revealed in her 2010 book William and Harry that Diana was resistant to the bold dress. However, Yahoo wrote, "In the end, the urge to make a statement as a newly single woman in bold clothing won out."

Diana chose Galliano, who had just been named head designer at Dior, and "had him create a special version of a midnight blue dress for the maison's first collection," Vogue reported. It was the ultimate fashion flex on a night when everyone's eyes were on you." The lingerie-inspired midnight blue silk slip dress with black lace trim was accompanied by a matching silk robe.

Of the 1996 Met look, Eloise Moran, author of The Lady Di Look Book, said, "That was one of the most stunning of her dresses: the Lady Di Look Book: What DIana Was Trying to Tell Us Eloise Moran, author of Through Her Clothes, told Yahoo. 'But I thought she looked fabulous. She looked so happy and confident." Moran said of Diana's decision to push the envelope through fashion, "I think she embraced it and enjoyed it. She knew she couldn't escape the attention and the spotlight, but I think she positioned it differently, not as a member of the royal family, but as an icon, like Marilyn Monroe, a huge international star. And I think the dress really reflected that."

It was, Moran says, the moment when Diana "went from royal to international celebrity." Was it the Revenge Look?" said Moran, who in addition to her book also runs the Lady Di Revenge Look Instagram account.

Despite her divorce, Diana chose to wear the iconic sapphire and diamond engagement ring. She also accessorized her outfit with sapphire and diamond cluster drop earrings and a sapphire and pearl choker necklace, made famous when she wore it to dance with John Travolta at the White House in 1985. The choker was made from a brooch given to Princess Diana on her wedding day in 1981, which she eventually turned into a necklace, "Bustle" reported.

During the event, Diana was escorted by Galliano and considered the "belle of the ball." Her newfound loyalty to Galliano and Dior would last, tragically, until the end of her life just eight months later. Elegant yet revealing," Galliano's work that evening "caused something close to a sensation and showed the newly divorced Diana in a racy new light, unbound by the rigid traditions of royal attire," wrote Newsweek magazine. The gown went on display at the Victoria and Albert Museum in London and became one of the most famous looks in the history of the Met Gala.

As pervasive as the Met Gala is in the culture, only one other member of the British royal family attended, and it was not Diana's daughter-in-law, the Duchess of Wales or the Duchess of Sussex. It was Princess Diana's niece, Princess Beatrice, who attended in 2018 wearing a purple Alberta Ferretti gown. Royalty from other countries, like Queen Rania of Jordan and Charlotte Casiraghi of Monaco, have attended the Met, and they have been named to special guest lists in the past.

Has Diana attended the Met Gala since her debut in 1996? Given her friendship with Gianni Versace, she would certainly have attended the Met Gala on December 8, 1997, after his indiscriminate murder in July 1997. However, just one month after attending Versace's funeral in Milan, Diana died in a car accident in Paris at the end of August, four months before the Met that year.