December 25, 1981
This sweet mohair teal coat from Bellville Sassoon featured the cutest green piping and puff sleeves—not to mention how the floral embroidery matched the flowers in her hands. Her pillbox hat, courtesy of John Boyd, paired perfectly.
December 25, 1982
Pink for Christmas? Yes, please! Princess Diana’s Jasper Conran look featured the best that ’80s fashion had to offer, from a vibrant hue to a playful pattern and skirt suit silhouette.
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December 20, 1983
At a Christmas concert in London, the princess wore a dark velvet dress with the sweetest lace collar—a delicate doily detail that was mirrored in her cuffs. The collar was a signature style for the royal, who had several from designers such as Bellville Sassoon.
December 25, 1983
This white skirt suit with red accents was perfect for a snowy Christmas.
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November 25, 1985
Attending the film premiere of Santa Claus in London, Diana pulled out the most elegant festive look. The two-toned blue ensemble, made from smooth velvet, featured a sheer lacy panel and long, flowing skirt. Her matching choker was the cherry on top, and she paired it all with sapphire and diamond studs. In another instance, she wore the same look with a tiara—which is definitely holiday-appropriate.
December 25, 1985
Seen alongside Queen Elizabeth II, Diana gave the classic muff a much needed update, pairing the furry black piece with a Marina Killery hat and an army jacket designed by Piero de Monzi in festive red. Plus, her black patent boots were the coolest snow boots.
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December 25, 1987
Diana’s yellow-on-yellow Escada coat completely redefined what Christmas colors could be, and her off-kilter Philip Somerville hat was the coolest royal alternative to the classic fascinator or pillbox style.
December 13, 1989
She may have been the people’s princess, but she was also the queen of mismatched prints. Taking sons William and Harry to a Christmas carol concert in London, she stepped out in a red-and-black look, composed of a classic check blazer and dotted maxi skirt. The best part? The young princes matched their mother in their school uniforms, which trimmed with red piping.
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December 25, 1994
Diana’s monochrome looks continued in 1994, when she pulled out the coziest teddy bear ensemble, with a fluffy hat that perfectly matched her cuffs. Balancing all the layers with a bit of leg, she paired the outerwear, which was pulled from Frank Russell’s high street label Mansfield, with a high-slit skirt and stepped out with a young Prince William for the Christmas Day service at Sandringham.
June 1, 1981
An honorable mention, as it was technically not a holiday look, had to be Diana’s iconic Rowing Blazers sheep sweater—which has become a staple of holiday season inspiration.
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