Princess Diana’s Most Iconic Holiday Fashion Looks
- - Princess Diana’s Most Iconic Holiday Fashion Looks
Rachel KingDecember 22, 2025 at 7:00 AM
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Princess Diana’s Most Iconic Holiday Fashion Looks Getty Images
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Not everyone likes Christmas. Princess Diana was one such person. As noted by author Simone Simmons in 2005’s Diana: The Last Word, Christmas was already a difficult time for the Princess of Wales as “the season reminded her of her mother’s departure,” and the Spencer family broke apart when Diana was a small child.
Her discomfort with royal holiday celebrations became well known within palace circles by the late 1980s, per Vanity Fair. Her former butler Paul Burrell told Marie Claire in 2024 that she found the experience “like a pressure cooker” but “had to grin and bear it” because “she knew that was her duty.”
It was no secret that the Princess of Wales dreaded the royal family’s Christmas gatherings at Sandringham, which was dramatized in Pablo Larraín’s 2021 film Spencer. “It was highly fraught,” Diana told biographer Andrew Morton in Diana: Her True Story in Her Own Words. “[It was] terrifying and so disappointing. No boisterous behavior, lots of tension, silly behavior, silly jokes that outsiders would find odd, but insiders understood. I sure was [an outsider].”
Despite her unhappy feelings, Diana continued to attend Sandringham Christmases even after her separation from Prince Charles in 1992 to be with her then-young sons, Prince William and Prince Harry. But after Charles and Diana formally divorced in 1996, the Princess of Wales vowed to “never again submit herself to the ‘ordeal’ of a royal Christmas,” Simmons wrote in The Last Word.
She often made the best of it, though, channeling her emotions and personality through fashion during the holidays. From vivid coat dresses to sharply tailored suits, her ensembles became her armor, projecting confidence even when she felt none. In the years since, her Christmas style has become legendary—graceful, expressive, and unmistakably her own. Here’s a look back at Princess Diana’s unforgettable holiday looks, which still inspire royal watchers and designers alike.
1981
Photo credit: Princess Diana Archive - Getty Images
Seen here walking down the steps of St George's Chapel at Windsor Castle with Prince Edward, Princess Diana was celebrating her first Christmas with the royals that December. Dressed in a billowy teal Bellville Sassoon coat embroidered with flowers and a matching pillbox hat, the new Princess of Wales was also pregnant with her first child, Prince William, at the time.
1982
Photo credit: Princess Diana Archive - Getty Images
Diana was pretty in pink in 1982 with this floral pink brocade skirt suit by Jasper Conran and matching oversized boater hat.
1982
Photo credit: Tim Graham - Getty Images
As patron of the Sir Malcolm Sargent Cancer Fund, the Princess of Wales attended a Christmas concert in London in a black velvet dress with a lace Peter Pan collar and pearl earrings.
1983
Photo credit: Anwar Hussein - Getty Images
Also on the steps of St. George’s Chapel, Diana wore a form-fitting cream modernist suit with a matching hat with red accents as she and Prince Charles chatted with a priest after the service.
1984
Photo credit: Georges DE KEERLE - Getty Images
Princess Diana had a beaming smile on her face as she arrived at St George's Chapel alongside Prince Charles and Princess Anne, who was walking with her son, Peter Phillips. This would have been one of Diana’s first public appearances since giving birth to Prince Harry on September 15, 1984.
1985
Photo credit: David Levenson - Getty Images
Arriving at the November 25 premiere of Santa Claus at the Odeon Leicester Square in London, the Princess of Wales wore a flowing midnight blue velvet gown by Catherine Walker.
1985
Photo credit: Anwar Hussein - Getty Images
Leaving St. Mary Magdalene Church after the Christmas Day service in 1985, Diana bundled up in a red military-style Piero de Monz coat with a black velvet hat by Marina Killery, a Russian-style muff, and black patent boots.
1987
Photo credit: Julian Parker - Getty Images
Holding the hand of a very young Lady Rose Windsor (now Gilman) dressed in a red coat, the Princess of Wales wore an oversized yellow checked Escada coat with a matching Philip Somerville hat at Windsor Castle.
1988
Photo credit: Tim Graham - Getty Images
Leaving the winter coat at home or in the car, Diana went for a high-fashion look with this angular hat—perhaps a modern take on the tricorne—with a tailored coat dress featuring very ‘80s neon blue contrasts on the collar and sleeves.
1989
Photo credit: Georges DE KEERLE - Getty Images
The Princess of Wales arrived at Wetherby School’s Christmas carol concert in London on December 13, 1989, with Prince William and Prince Harry in this festive red and white ensemble.
1990
Photo credit: Tim Graham - Getty Images
Smiling during a walkabout at Sandringham with Prince William on December 23, the Princess of Wales sported a red-and-white houndstooth Moschino jacket with a black turtleneck and wide-brimmed red hat.
1990
Photo credit: Princess Diana Archive - Getty Images
Shunning red and green, Diana wore a purple Bellville Sassoon coat dress with a striped collar and matching sleeves, paired with a wide-brimmed hat by Philip Somerville.
1991
Photo credit: Martin Keene - PA Images - Getty Images
Wearing a red and pink Catherine Walker dress, the Princess of Wales attended a Joy to the World Christmas concert at the Royal Albert Hall in London on December 17, 1991 with Prince William and Prince Harry.
1991
Photo credit: Princess Diana Archive - Getty Images
Queen Elizabeth always knew how to stand out in a crowd with color. Diana knew how to stand out in other ways. Sandringham is known to be chilly on December 25, and with everyone else bundled up, that was likely the case in 1991. That didn’t stop the Princess of Wales from wearing this blue turquoise skirt suit that looks ready for spring.
1993
Photo credit: Mirrorpix - Getty Images
Red plaid is always acceptable at the holidays. (Maybe only acceptable at the holidays.) The Princess wore this bright blazer with a silk black scarf as she switched on the twinkling lights at Bond Street in central London.
1993
Photo credit: Princess Diana Archive - Getty Images
In what has arguably become her most iconic Christmas look, Diana wore a red double-breasted coat with a black hat and veil—a look that later inspired one of Kristen Stewart’s ensembles in Spencer.
1994
Photo credit: Princess Diana Archive - Getty Images
In what would be Diana’s last walkabout at Sandringham, the Princess of Wales bundled up once more in a faux fur–trimmed Mansfield coat with a matching hat, seen here with Prince William.
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