15 of Princess Diana’s Most Iconic Fashion Moments
These timeless looks are fit for a princess!
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.
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.
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.
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.
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.
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.
Show a little shoulder (but just one)
Diana gravitated toward one-shoulder gowns that showed a little skin while staying modest.
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.
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.
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.
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.
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.
Beyond plain black tights
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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.
Bring back old trends
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To visit her nation’s troops in 1995, Diana wore a pink skirt suit and pillbox hat à la Jackie O.
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. Next, look at these rarely seen photos of Princess Diana with Prince Harry.