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15 of Princess Diana’s Most Iconic Fashion Moments

These timeless looks are fit for a princess!

Charity Dinner at the Serpentine Gallery, Hyde Park, London, Britain - 1994NILS JORGENSEN/Shutterstock


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.

Ibrahim Babangida, the Nigerian President, gives Banquet at Claridges Hotel, London, Britain - May 1989Nils 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. 

Prince Charles and Princess Diana tour of Japan - 1986JOHN 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.

Royal Tour of Wales, Britain - Nov 1982Shutterstock

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 ring stands out against the red of the coat.

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

Britain Prince Charles, London, United KingdomJohn 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.

VARIOUS Princess DianaShutterstock

Show a little shoulder (but just one)

Diana gravitated toward one-shoulder gowns that showed a little skin while staying modest.

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

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.

British Royal Tour of Australia - 1983OHN 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.” This is how Princess Diana spent the final week of her life.
Royal Tour Visit Of Australia - 1983JOHN 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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