15 of Princess Diana’s best winter fashion looks

  • Princess Diana is known for her stylish and daring fashion looks that stand the test of time.
  • From midi skirts worn with boots to puffer jackets over leggings, many of her wardrobe choices are still on-trend today.
  • We looked back at the royal’s most fashionable cold-weather outfits, including elegant plaid coats and winter white gowns.
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Princess Diana’s style continues to inspire us — and many of her looks are still on-trend today.

From bold plaid prints to brightly colored sweaters and tailored coats, Princess Diana always knew how to make a statement with her outfits. With the chilly winter months quickly approaching, it’s no wonder we wanted to remember some of the royal’s most iconic cold-weather fashion moments.

Here are 15 of Princess Diana’s best winter fashion looks.

A 19-year-old Lady Diana Spencer was photographed wearing a colorful yet casual winter sweater, a white turtleneck, khaki-colored corduroy pants, and green rain boots after her engagement to Prince Charles was announced.

princess diana winter fashion

Princess Diana and Prince Charles at Craigowan Lodge, Balmoral Estate in 1981.
Tim Graham Photo Library/Getty Images


This look is definitely casual for the soon-to-be princess but is one of her more notable fashion moments. Fair Isle and Aztec-inspired sweaters were very on-trend in the 80s, as was corduroy — which remains popular in current fall and winter trends.

During a visit to the Royal Opera House in December 1981, Diana looked glamorous in a pure white coat, pearl jewelry, and her world-famous sapphire engagement ring.

princess diana winter fashion

Princess Diana during a visit to the Royal Opera House in December 1981.
Tim Graham Photo Library/Getty Images


After the death of Princess Diana in 1997, Prince William would later gift the ring to his fiancée, Kate Middleton. Diamonds from Princess Diana’s private collection were also used in the making of Meghan Markle’s engagement ring, along with a diamond from Botswana, where she and Prince Harry vacationed.

Princess Diana, age 20, wore a festive, bright red coat with a matching hat before Christmas in 1981.

princess diana winter fashion

Prince Charles and Diana during a visit to Guildford Cathedral.
David Levenson/Getty Images


The princess’ hat also came fitted with a sheer red veil, adding another element of royal glamour to her look.

Princess Diana made an accidental faux pas during her first Christmas as a royal when she gifted Princess Anne a cashmere sweater instead of the traditional “gag gift” the royals exchange on Christmas Eve. 

This cozy, pink-hued winter coat looked stunning on Princess Diana.

princess diana winter fashion

Diana, Princess of Wales wearing Bellville Sassoon maternity coat, in Huddersfield, UK, 1982.
Terry Fincher/Princess Diana Archive/Hulton Royals Collection/Getty Images


The feminine collar was on-trend at the time, when big-shouldered silhouettes dominated the 1980s’ fashion trends. While this winter coat might not match today’s more minimalist styles, it certainly looked beautiful on Princess Diana as she met with subjects in Huddersfield. 

Princess Diana looked effortlessly chic in this collared, plaid tan coat with a matching hat.

princess diana winter fashion

Diana, Princess of Wales, wearing an Arabella Pollen coat on a visit to Wales in November 1982.
Jayne Fincher/Princess Diana Archive/Hulton Royals Collection/Getty Images


This outfit is quintessentially chic and European, from the puffy beige beret to the plaid print on the princess’ coat and classic button detailing. This monochromatic look fits perfectly with current winter fashion trends.

Princess Diana looked prim and proper in this tan tie-belted coat.

princess diana winter fashion

Princess Diana wearing a Caroline Charles coat during a visit to the Wandsworth DHSS office in December 1982.
Jayne Fincher/Getty Images


Meghan Markle has also worn a similar camel-colored coat, showing that classic pieces never go out of style. Both Kate Middleton and Meghan Markle have paid homage to Princess Diana’s style over the years, and this tan coat is one of the more memorable examples.

When Princess Diana arrived at Gloucestershire Cathedral for a Christmas service wearing a Cossack-style hat and muff, the world took notice.

princess diana winter fashion

Princess Diana arriving at Gloucestershire Cathedral for a Christmas service.
Tim Graham Photo Library/Getty Images


From her mahogany leather boots to the fur hat and cozy hand muff, Princess Diana truly embodied winter fashion with this look. Today, the British royals still go the extra mile when it comes to their Christmas church service looks. 

Princess Diana looked classically stylish — yet very ’80s — in this winter coat look.

princess diana winter fashion

Princess Diana in Hamburg wearing a coat designed by Arabella Pollen and a faux fur beret style hat.
Tim Graham Photo Library/Getty Images


The coat was designed by Arabella Pollen and is trimmed with faux fur on the collar and cuffs. The people’s princess also wore a faux fur beret to complete her festive look.

Princess Diana was a vision in winter white while wearing this cowl-necked sweater, white skirt, red patent leather boots, and matching belt.

princess diana winter fashion

Princess Diana in Kensington Palace gardens in December 1983.
Anwar Hussein/WireImage/Getty Images


Midi-length skirts paired with boots are still popular today, proving the princess knew her way around a timeless fashion look.

In January 1985, Princess Diana went skiing in Liechtenstein wearing a cozy blue-and-white knit hat and a stylish red ski jacket.

princess diana winter fashion

Princess Diana during a skiing holiday in Liechtenstein in January 1985.
Georges De Keerle/Getty Images


Princess Diana’s casual holiday style sets her apart from the rest of the royal family. 

Princess Diana looked sophisticated in a beige Caroline Charles coat in February 1985.

princess diana winter fashion

Diana, Princess of Wales, during a visit to Derby, UK, in February 1985.
Jayne Fincher/Princess Diana Archive/Getty Images


Long mid-length coats with tall boots are a recurring trend this winter, and Diana perfectly matched her boots and her handbag. Diana also wore a statement hat the same color as her coat in classic royal style. 

On another ski trip, Princess Diana took to the slopes wearing this very ’80s striped puffer jacket, a white turtleneck, and mirrored sunglasses.

princess diana winter fashion

Princess Diana during a skiing holiday in Klosters, Switzerland, in March 1988.
James Andanson/Sygma/Getty Images


1980s-inspired styles like windbreakers and neon are a major trend this winter. While Princess Diana’s sunglasses style was popular in the ’80s, large black shades or bright-colored sunglasses are the predicted eyewear trends for this season.

This yellow plaid coat and matching hat are perfect for chilly winter days.

princess diana winter fashion

Princess Diana visits Cowes to christen the boat “Vigilant,” a fast cruiser of the British Customs Service, in 1988.
Tim Graham Photo Library/Getty Images


Plaid prints come back as a popular trend practically every fall and winter season. Plaid blazers and jackets are in this winter, as are festive plaid skirts and dresses for the holiday party season. While Princess Diana wears a more minimalist plaid print, busier ’70s-inspired prints are more on-trend this year. 

While attending the “Winter Garden” opera in February 1989 in New York City, Princess Diana wore an embroidered white-and-gold gown and matching jacket.

princess diana winter fashion

Princess Diana during “Winter Garden” opera on February 2, 1989, in New York City.
Ron Galella/Ron Galella Collection/Getty Images


While on a visit to New York City in 1989, Princess Diana sported a Victor Edelstein gown to a gala dinner at the World Financial Center’s Winter Garden. While some say you should never wear white after Labor Day, we highly disagree and are adamant fans of “winter white,” with a touch of royal sparkle.

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