Royals

Diana, Princess of Wales  (1961 - 1997) during a skiing holiday in Lech, Austria, 29th March 1992.  ...
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20 Of Princess Diana’s Best Winter Looks

Her hat selection alone.

During Princess Diana’s all-too-brief time as a senior member of the royal family, she managed to be so many things to so many people. A mother to two sons Prince William and Prince Harry, wife to Prince Charles. A trailblazing philanthropist, a passionate activist. Even after all these years, she is still remembered for all of these amazing qualities. And let’s be honest, her iconic fashion sense. As the snow falls and we all have to consider wardrobe changes, let Princess Diana’s best winter looks be everyone’s guide to keeping it chic when it’s cold outside.

Lady Diana Spencer was just 19 years old when she got engaged to Prince Charles, future King of England, but already she had a strong sense of her own style. She knew what she liked, knew what made her feel comfortable, and always knew how to make her clothes speak for her. Elizabeth Holmes, author of the book HRH: So Many Thoughts On Royal Style, once told Insider, “I think Diana's choices were screaming sometimes. Diana delighted in clothes. Her story is filled with such highs and lows, but understanding her fashion, how she used it, found power in it, and reclaimed her voice is my favorite part of this book.”

Princess Diana’s best fashion looks for winter spoke volumes... now let’s figure out what they were trying to say. Here are 20 of her best looks from over the years.

A Festive Cardigan

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Princess Diana was still working at a local nursery school in November 1980 and dressed the part. A festive cardigan, ruggled blouse, and a hurried walk through the streets of London say it all.

Loving The Outdoors

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The newly engaged Prince Charles and Princess Diana posed for photos at Balmoral Castle in Scotland. Princess Diana’s look of colorful sweater, turtleneck, cords, and Hunter boots are still worn by everyone today.

A Red Veil Is Everything

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Princess Diana wore a red veiled hat with a matching collared jacket and blouse to Guildford Cathedral with new husband Prince Charles in December 1981. The hat helped with her trademark shy smile.

Standing Out In The Crowd

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In 1985, Princess Diana joined the rest of the royal family for Christmas at Sandringham Estate. And she stood out with no problem in a double-breasted red wool coat and a black muff to keep her hands warm.

Head To Toe Burgundy Velvet

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In February 1990, Princess Diana wore a burgundy midi skirt with matching velvet blazer and cream turtleneck. She also wore heels in the grass, a brave move.

The Original Snow Princess

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Rarely did Princess Diana look cooler than when she was skiing, and this look from a ski holiday in Lech, Austria in 1993 was one of her best. I can’t decide if it’s the hair, the giant white mittens, or the one-piece snowsuit. It all works.

Her Mom Look

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In 1989, Princess Diana mixed prints with a checked blazer and floral burgundy skirt, but of course she looked great. And happy, she was taking her two sons to Wetherby School in their little matching uniforms.

Matching With Santa

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Princess Diana wore a winter white skirt suit to meet Santa Claus at a children’s hospital in 1987, creating the perfect foil for his red outfit.

Red Boots For Christmas

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Princess Diana’s winter white cowl neck sweater and skirt were offset by red boots and a belt for Prince William’s first Christmas.

Iconic In Brown Suede

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Princess Diana joined sister-in-law Sarah Ferguson for a ski holiday in 1988, and her brown suede skirt and slouchy boots were the perfect winter travel outfit.

Christmas With The Kids

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Princess Diana’s short boots were the perfect pairing with her long brown coat and fur hat for Christmas Day with her sons in 1994.

Sleighing All Day

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During a sleigh ride with Prince William and Prince Harry in 1993, Princess Diana wore a black leather coat and a denim shirt. Not the usual royal uniform, but she was not a usual royal.

Happy At Home

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In this photo from December 1990 at Kensington Palace, Princess Diana looks adorable in her baby blue skirt and sweater combo. That puppy isn’t hurting things either.

Loving A Winter Tartan

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In February 1990, Princess Diana wore a red tartan blazer during a royal outing and looks spectacular.

Pregnant In A Cape

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In February 1982, pregnant Princess Diana topped her red evening gown with a full black cape. That’s a perk of being a royal; capes are an actual thing.

Coolest School Drop-Off Look

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Polka dot tights? Over-the-knee boots? A bright blue scarf? Princess Diana’s school drop off outfit in 1986 was the one to beat.

Going For Gold

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Christmas 1987 at Windsor saw Princess Diana’s boldest Christmas look. A gold and black patterned coat nipped in at the waist, tall black boots and a jaunty hat. Love it.

Strong Looks For Mom & Son

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Princess Diana and Prince William were the real power couple in February 1986. Her dramatic red coat looked great with his bright blue wool coat. Also check out his gloves.

Another Strong Coat Look

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The genius of this bright blue coat worn by Princess Diana in 1989 was that it was a statement all its own. No accessories needed.

A Fresh Start

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By January 1996, Princess Diana and Prince Charles had separated. She was no longer a senior member of the royal family. And this photo of her covering up her workout clothes, complete with sneakers and socks, is a glimpse at the life she was starting to lead.