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15 of Princess Diana’s Most Iconic Fashion Moments

These timeless looks are fit for a princess!

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Charity Dinner at the Serpentine Gallery, Hyde Park, London, Britain - 1994


Princess Diana always knew how to make a black dress look classy. Soon after Prince Charles confessed he’d been unfaithful to her in a 1994 interview, Princess Diana attended a Vanity Fair party in an off-the-shoulder little black dress, paired with black tights and a statement necklace. She looked so strikingly sexy that the outfit has gone down in history as her “revenge dress.” These are surprising facts you never knew about Princess Diana.
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Ibrahim Babangida, the Nigerian President, gives Banquet at Claridges Hotel, London, Britain - May 1989
Nils Jorgensen/Shutterstock

Bright patterns

Princess Diana wore this gorgeous floor length, pink silk gown in 1989 to a banquet in London. She paired it with a necklace, earrings, and a statement tiara. Speaking of tiaras—read the story behind the Spencer Tiara, one of Princess Diana’s favorite tiaras.

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Prince Charles and Princess Diana tour of Japan - 1986
JOHN SHELLEY/Shutterstock

Creative necklaces

Who says a necklace has to rest on your collarbone? Diana found unique ways to wear her jewelry. In 1985, she wore an emerald choker of Queen Mary’s around her head as a headband on one occasion and let a pearl necklace fall backward between her shoulders to accentuate a backless dress at another. Check out these stunning, rarely seen photos of Princess Diana.

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Royal Tour of Wales, Britain - Nov 1982

Colorful coat

On a royal tour of Whales in 1982, Princess Diana stepped out in this gorgeous wool coat and blue hat. You can see how her sapphire engagement ring stands out against the red of the coat. Browse these photos of young Princess Diana before she became the People’s Princess.

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Prince Charles and Lady Diana Spencer, Scotland, Britain - May 1981
Photonews Scotland/Shutterstock

Function and style

Crummy weather shouldn’t keep you from looking your best. In her pre-wedding photos with Prince Charles, Diana wore green Hunter rain boots. The brand has seen a surge in popularity again in recent years, probably because they’re classic, timeless, and durable. Browse these pictures of Prince Charles and Princess Diana’s wedding.

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Britain Prince Charles, London, United Kingdom
John Redman/AP/Shutterstock

Flowy dress

After giving birth to Prince William, Princess Diana stepped out in a flowy polka dot dress. Kate Middleton left the hospital in a similar looking dress after giving birth to her first child. Check out these other times Princess Diana and Kate Middleton basically wore the same outfit.

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VARIOUS Princess Diana

Show a little shoulder (but just one)

Diana gravitated toward one-shoulder gowns that showed a little skin while staying modest. Here are some of the most inspiring Princess Diana quotes.

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Wedding of Prince Charles and Lady Diana Spencer, London, Britain - 29 Jul 1981

Statement sleeves

Princess Diana was the queen of statement sleeves—a popular ’80s trend that can be seen in some of her most iconic looks. The gravity-defying poufy sleeves can be seen on her wedding dress.

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British Royal Tour of Australia - 1983
OHN SHELLEY/Shutterstock

Princess look

Diana wasn’t afraid to look like a girly girl, fully embracing her “princess” title. “At the beginning, her look was very ‘fairytale princess.’ There were lots of bows and frills,” Kerry Taylor, whose auction house auctioned ten of Diana’s dresses in 2013, has said. “She was the embodiment of every little girl’s fantasy of what it meant to be a princess.”
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Royal Tour Visit Of Australia - 1983
JOHN SHELLEY/Shutterstock

Bold patterns

Princess Diana didn’t shy away from bold outfits. She is seen here wearing a red and white polka dot patterned dress, a bright red blazer to match, and a white hat and red shoes.

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Tim Rooke/Shutterstock

Pairing casual with polished

Diana is known for her fancy dresses and gowns, but she could work a dressed-down look, too. She paired a collared white shirt with light wash jeans when on a trip to Bosnia in 1997.
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Richard Von Weizsacker state visit, banquet at the German Ambassador's residence, London, Britain - Jul 1986

Gold accents

It’s hard to forget this strapless white and gold evening gown that Diana wore to a banquet in 1986. The long white gloves make her look especially poised. These are the secrets no one knew about Princess Diana until after her death.

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Prince & Princess Of Wales- Visit Australia & Usa 5th October 1985 (divorced 8/96). (princess Diana Died 31/8/97). Royal Tour: Australia Stockings Worn By Princess Diana During Her Day At The Races - Melbourne Cup...royal Visits
James Gray/Daily Mail/Shutterstock

Beyond plain black tights

Black stockings are a classic way to make an outfit more modest, but Diana pulled off unexpected twists on tights. At the 1985 Melbourne Cup, her black tights featured back seams that stretched through bow motif above the ankle, and on another occasion, she went monochromatic by wearing blue tights with a blue skirt.

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Diana Princess Of Wales Arrives For Inspection Of 2nd Battalion Of The Princess Of Wales Royal Regiment At Howe Barracks Canterbury Kent.
Keith Waldegrave/Associated Newspapers/Shutterstock

Bring back old trends

To visit her nation’s troops in 1995, Diana wore a pink skirt suit and pillbox hat à la Jackie O.

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Various Princess Diana - circa 1981
Kip Rano/Shutterstock

Floral dress

Princess Diana looked gorgeous in this floral printed dress with a white blazer draped over her shoulders. Such a simple look is still in style today.

Marissa Laliberte
Marissa Laliberte-Simonian is a London-based associate editor with the global promotions team at WebMD’s Medscape.com and was previously a staff writer for Reader's Digest. Her work has also appeared in Business Insider, Parents magazine, CreakyJoints, and the Baltimore Sun. You can find her on Instagram @marissasimonian.