Though Princess Diana was not only a part of the fashion conversation but a leader of the fashion conversation for most of her public life—from her July 29, 1981 wedding day to Prince Charles until her death on August 31, 1997—she only attended one Met Gala, attending the event on December 9, 1996. (Anna Wintour had just assumed chairmanship of the event the year prior, in 1995, though she didn’t chair it in 1996, in favor of fellow magazine editor Liz Tilberis; since its formation in 1948 the Met was always exclusive and a hot ticket—but it hadn’t yet reached its peak “first Monday in May” fever pitch.)
December 9, 1996 found Diana just under three months removed from her divorce from Charles being finalized that August 28. The 1996 Met paid homage to the late fashion designer Christian Dior, a house with which the Princess of Wales had a friendly relationship—Dior had even renamed its 1994 handbag previously known as Chouchou to Princese to honor Diana; eventually, it would become Lady Dior, named in honor of Diana’s title before marriage, Lady Diana Spencer. Naturally, at the Met Diana carried a Lady Dior, which she did often since first being introduced to the style in 1995.
At Diana’s one and only Met, her star power was intoxicating. She arrived at the Metropolitan Museum of Art on the arm of Tilberis, who was co-chairing the gala that night. Tilberis succeeded Wintour as editor-in-chief of British Vogue in 1987 and eventually became editor-in-chief of Harper’s Bazaar in 1992; the next year, she was diagnosed with ovarian cancer and died of the disease in 1999. Diana and Tilberis had become close after the two “formed a working relationship and then friendship” with Diana during her years at British Vogue, and, in 1995, Diana made a special visit to New York City to present Tilberis with a Council of Fashion Designers of America (CFDA) award. Per Newsweek, Tilberis invited Diana to the Met in 1996, and had become “a powerful ally of the princess during her separation from Prince Charles”; as Tilberis battled cancer, Diana would often call and write to her to give her words of encouragement and comfort, of course never knowing that her life would but cut short two years before Tilberis’ own.
Because of her relationship with both Tilberis and Dior, the temperature was right for Diana to make her Met debut. “The royal made a discreet entrance,” Vogue writes, “while wearing her most un-royal look to date.” Diana’s “inky silk John Galliano for Dior slip dress, with its lace negligée trim and matching dressing-gown style robe, was eons away from the Di who once charmed the world with her sheep jumper, and signaled that the recent divorcée was enjoying a new phase of her life unshackled from Kensington Palace protocol,” Vogue continues. The lingerie detailing almost stopped the look from happening at all: royal biographer Katie Nicholl revealed in her 2010 book William and Harry that Diana had reservations about the daring dress—mostly that it might embarrass her elder son, Prince William, who was 14 at the time and struggling with his parents’ split. But, Yahoo writes, “ultimately, the urge to make a bold sartorial statement as a newly single woman won out.”
Diana chose Galliano—who had just become head designer of Dior—“to make her a special version of a midnight-blue dress for his first collection for the maison,” Vogue reports. “It was the ultimate fashion flex on a night when all eyes were watching.” The lingerie-inspired midnight blue silk slip dress with black lace trim, accompanied by its matching silk robe—perfect to help ward off the December chill in New York City and provide a bit of modesty—was considered the followup, if you will, to her infamous 1994 Christina Stambolian “revenge dress,” worn about two years after Charles and Diana’s separation in 1992.
Of the 1996 Met look, “That was one of her most shocking dresses,” Eloise Moran, author of The Lady Di Look Book: What DIana Was Trying to Tell Us Through Her Clothes, told Yahoo. “But I thought she looked fabulous. She just looks so happy and confident.” Moran added of Diana’s decision to push the envelope through fashion “I think she was embracing it and enjoying it. She knew she could never get rid of the attention and the spotlight on her, but I think she was positioning it in a different way, as a kind of international megastar, Marilyn Monroe-type icon rather than a member of the royal family. And I think the dress really reflected that.”
It was the moment, Moran said, that Diana went “from royal to international celebrity.” Was it a revenge look? Moran—who, in addition to her book, also runs the Lady Di Revenge Looks Instagram account—said, simply, “100 percent.”
Divorced though she was, Diana still opted to wear her iconic sapphire and diamond engagement ring, which the current Princess of Wales, Catherine, now wears. She further accessorized the outfit with sapphire and diamond cluster drop earrings and a sapphire and pearl choker necklace that was made famous by its appearance during her 1985 dance with John Travolta at the White House. Driving home the point, the choker also made an appearance in 1994, when she debuted that famous revenge dress look; it was originally built from a brooch gifted to her by the Queen Mother on Diana’s 1981 wedding day, and Diana eventually had it made into a necklace, Bustle reports.
Inside the event itself, Diana was accompanied by Galliano, and was deemed the “belle of the ball.” Her newfound loyalty to Galliano and Dior—which would continue until the end of her life, tragically just eight months later—as well as Chanel and Versace signaled a shift as Diana moved away from British fashion houses and away from the monarchy. “The elegant, but revealing” Galliano creation that night “caused a near sensation, showing the newly divorced Diana in a risqué new light, unburdened by the staid traditions of royal dress,” Newsweek writes. Always adept at sending sartorial messages effectively, the gown is now a part of fashion history, even going on display at London’s Victoria and Albert Museum and becoming one of the most well-known looks in Met Gala history.
As pervasive as the Met is to culture, only one other British royal has attended—and it’s not either of Diana’s daughters-in-law, the Princess of Wales or the Duchess of Sussex. It’s Princess Beatrice, Diana’s niece, who attended the event in 2018, wearing a purple Alberta Ferretti gown. Royals from other countries do attend the Met on occasion, like Queen Rania of Jordan and Monaco’s Charlotte Casiraghi, both of whom have made the exclusive guest list in the past.
Would Diana have attended Met Galas in the future after her debut appearance in 1996? Considering her close friendship with Gianni Versace—who was honored at the 1997 Met after his senseless murder that July—she would have no doubt been on hand for the occasion on December 8, 1997. But, just one month after attending Versace’s funeral in Milan, Diana was killed in a car accident in Paris at the end of August, four months before that year’s Met, leaving us all wondering what might have been for her—in terms of the Met and beyond.
