How Princess Diana’s Showstopping 1987 Cannes Dress Honored Her Mentor Grace Kelly: Inside Their Bond

When Princess Diana graced the 1987 Cannes Film Festival alongside Prince Charles for a fleeting ten-hour visit, her choice of a strapless blue tulle gown was far from accidental.

The exquisite creation served as a poignant homage to another glamorous, world-famous royal, Princess Grace of Monaco, a figure who had become a royal mentor of sorts to Diana and who had tragically died five years prior in a car accident. This fate would, with heartbreaking irony, befall Diana just a decade later in 1997.

Back in 1987, Diana strategically chose Catherine Walker, a designer who would become synonymous with her most iconic looks, as she and then-Prince Charles attended the prestigious film festival to champion the British film industry.

Diana’s soft blue dress was elegantly accompanied by a matching chiffon scarf that looped around her neck and billowed out behind her as she walked. This dramatic accoutrement added a sense of ethereal movement to the gown, “catching the breeze that was high on the evening of the film screening,” according to Newsweek.

Cannes held a particularly significant connection to the late Princess Grace; it was on the French Riviera that she, then simply an American movie star, first met her future husband, Prince Rainier, in April 1955, almost exactly a year before their fairytale wedding in April 1956.

The creative connection between Princess Diana and Walker drew inspiration from a blue Edith Head gown famously worn by the Academy Award-winning Kelly in Alfred Hitchcock’s iconic 1955 film, To Catch a Thief, which, fittingly, was shot on the French Riviera.

Much like Diana’s deliberate decision to recreate its essence, the almost glacial shade of blue was intentionally chosen for Grace’s character, Frances Stevens. As Hitchcock himself explained in a 1962 interview: “I deliberately photographed Grace Kelly ice-cold and I kept cutting her profile, looking classical, beautiful and very distant.”

Fast-forward to 1987, Diana completed her carefully considered look with flat baby blue shoes (which, according to the new 2025 Cannes Film Festival dress code, would be against protocol for women on the red carpet), elegant aquamarine and diamond chandelier earrings and a matching bracelet.

Diana’s connection with Kelly dated back to March 1981, shortly after announcing her engagement to Prince Charles and months before their highly publicized wedding on July 29th of the same year.

In his biography Once Upon a Time: Behind the Fairy Tale of Princess Grace and Prince Rainier, J. Randy Taraborelli recounts a deeply human moment between the two princesses. He reveals that Diana, overwhelmed by the enormity of her impending royal life, “burst into tears in front of Grace” while they touched up their makeup in the ladies’ room at a royal engagement.

As she stood on the precipice of marrying into the intensely scrutinized royal family in just four months, Diana, Taraborelli wrote, “foresaw a life totally devoid of privacy. She was frightened. What could she do? She was certainly asking the right woman for advice. Grace had always known how to use her celebrity to her advantage, whereas Diana seemed to shrivel under the spotlight’s glare.”

Grace, then 51 to Diana’s youthful 19, offered her younger royal counterpart a comforting embrace. She patted her shoulder before gently cupping Diana’s face in her hands, offering a prescient piece of advice: “Don’t worry, dear,” Grace said with a knowing air. “You see, it’ll only get worse.”

The bond between the two women, though perhaps brief, was clearly significant. When Grace tragically died in September 1982, Diana insisted on attending her funeral in Monaco, a testament to their connection, even though Diana had given birth to her firstborn, Prince William, a mere three months earlier, and against Prince Charles’ wishes.

Diana found Grace “wonderful and serene,” she confided in her biographer Andrew Morton, but with a perceptive insight, added that “there was troubled water under her. I saw that.”

Diana’s fashion choices were rarely arbitrary; they often conveyed profound meaning without uttering a single word. Her Cannes look was a masterful example of this sartorial storytelling.

The Princess of Wales’s heartfelt tribute to Kelly “didn’t go unnoticed,” and as Tatler reported, “as with all of Diana’s looks, a lot of thought and preparation had gone into the moment.”

The blue Catherine Walker gown enjoyed further moments in the spotlight. Diana re-wore the elegant design just two years later, to the 1989 premiere of the musical Miss Saigon.

Demonstrating both her sentimental attachment and her astute understanding of her iconic status, she later chose the Cannes gown to be part of her groundbreaking 1997 Christie’s auction, where she famously sold off 79 of her most memorable dresses.

The gown fetched an impressive $70,700 in 1997 and was subsequently put up for auction again in 2011, eventually selling for over $132,000 in 2013.

In a moving homage to her enduring legacy, the dress was displayed in 2017 at Diana’s former home, Kensington Palace, as part of a special exhibition commemorating the 20-year anniversary of her passing.