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How Princess Diana’s Hats Were a Secret Window into Her Life

Princess Diana was a true style-setter, so much so that many of her iconic looks were copied during her lifetime and continue to be fashion inspirations two decades years after her tragic death at age 36. Here, we focus on her hats and other headwear.

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floppy black hat
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Floppy black hat

In 1971, long before she held the title of “Princess,” a pre-teen Diana Spencer looked fashionable in a floppy-brimmed beachy hat. “The future Princess Diana was ‘boho chic’ way before it was all the rage,” points out Stephanie Bell of Famous Ladies Hats. We found one that looks almost exactly the same, which Bell suggests pairing with jeans, a flowing top with bell sleeves, and suede bootie. Here are some wonderful fashion tips we’ve learned from Princess Diana’s enduring style.

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white lace trimmed fascinator
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White lace-trimmed fascinator

This lace-trimmed white pillbox fascinator is just like the one the then Lady Diana Spencer wore to the Royal Ascot in Berkshire on June 16, 1981. Her marriage to Prince Charles was just five weeks away. Turns out lace is a white-hot trend for women today, especially when it comes to fascinators, we learned from Bell, who styles many women who are looking for precisely that look for events including the Kentucky Derby. “Fascinators have become extremely popular due to coverage of royal family weddings and special events. They can be worn year-round without the full commitment of wearing a hat and messing up your hair.” Find out the true story of what happened between Princess Diana and Prince Charles.

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lovers knot tiara
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Cambridge Lover’s Knot Tiara

The Cambridge Lover’s Knot Tiara was so heavy it hurt Princess Diana’s head, which is why she didn’t wear it at her wedding. But it became one of her favorite tiaras, and she was photographed in it many times. After Diana and Charles divorced, this tiara was returned to the Queen. It was not worn publicly again until 2015 when Kate Middleton wore it at a diplomatic reception at Buckingham Palace.
This costume-jewelry version is meant to look like the Cambridge Lover’s Knot Tiara, and Malacsina believes it still makes a beautiful choice for a bride, either with or without a veil. Check out these 19 times Princess Diana and Kate Middleton basically wore the same outfit.

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blue pillox lace fascinator
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Baby blue lightly-veiled pillbox fascinator

“Princess Diana was known to flash a demure smile and a shy gaze beneath her veil,” Bell tells Reader’s Digest. During both of her pregnancies (1982 and 1984), Princess Diana was seen wearing small, lightly veiled fascinators. Veils today add a flirty twist by adding a bit of mystery and style,” she adds.

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jeweled headband choker
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Jeweled headband/choker

“The mid-1980s was a very popular time for headbands,” Bell recalls. It started with the aerobic fitness craze, but in 1985, Princess Diana wore a diamond-and-emerald choker (a gift from the queen) as a headband, taking headbands to a more glamorous level. Even today, “Celebrities are loving these headbands to add to their messy, tousled hair updos on the red carpet,” adds stylist Christina Fortier. “These allow you to have as messy of hair as you like because that sparkle makes it all look and feel intentional.”

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blue pillbox fascinator
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Simple blue pillbox fascinator

In the spring of 1986, Princess Diana and Prince Charles headed to Canada to celebrate Canada Day. Photographs of Princess Diana in the simple, blue pillbox-style fascinator she wore with a houndstooth-print dress at a reception at Swy-A-Lane Park in Nanaimo, British Columbia on May 1 were reproduced in newspapers and magazines all over the world, cementing this as of Diana’s most iconic looks. It also happens to recall the “Jackie look” (as in Jackie Kennedy). “All that’s missing are large sunglasses,” Malacsina points out. “And it’s still a classic look.”

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mad hatter hat
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Mad Hatter-style hat

This hard-to-find hat looks a lot like the one Princess Diana wore at the VJ Day Commemoration in 1995, which she attended with Prince Charles, Prince William, and Prince Harry, except Diana’s was navy and white, and this one is black and white. “This style hat was one of those that really showcases the time period,” explains Malacsina. “It’s a conservative style that can be modernized by pairing it with wide leg pants and a simple blouse.”

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cathedral length veil
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Cathedral length bridal veil

Princess Diana’s wedding gown had a 25-foot train, but that was nothing compared to her 153-yard tulle veil, which was connected to her tiara (the Spencer Family Tiara). “This happens to be one of the most iconic fashion pieces in all fashion history,” Lauren Malacsina, a fashion stylist/designer based in Miami, tells Reader’s Digest. “The handmade lace is exquisitely done and its compliments her wedding dress.” In terms of trying out the look, yourself, Afa Ah Loo, a stylist with Jane.com, points out that while a super-long cathedral length veil is a showstopper all on its own, “a full-length ball gown with layers of tulle and hand beading might add even more drama.” The veil pictured is custom, so you can order it to be made as long as you’d like.

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pale broad brimmed
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Pale, broad-brimmed, be-ribboned fascinator

This pale, broad-brimmed, be-ribboned fascinator is a lot like the one Princess Diana wore when she attended the wedding of the Duke of Hussey’s daughter in May 1989 in Bath, England with Prince Charles, Prince William, and Prince Harry. It’s a classic “Di look,” Malacsina says, “and it’s one of my personal favorites, bringing to mind Marlene Dietrich and Lauren Bacall in a classic pantsuit eluding power.” It’s still a timely style that can be paired just as easily with a dress or a pair of wide-leg pants and a lace blouse. Check out these fascinating facts about Princess Diana you never knew.

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embroidered dupatta
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Embroidered dupatta

From September of 1995 until July of 1997, Princess Diana was involved in a romantic relationship with Hasnat Khan, a Pakistani heart surgeon. She reportedly adored him and also embraced his culture. Many believed she would have left the United Kingdom to join him there if the relationship had not ended. This embroidered chiffon scarf is called a “dupatta” and is a traditional South Asian head covering like the one Diana wore in Pakistan. Next, don’t miss these stunning, rarely seen photos of Princess Diana.

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Lauren Cahn
Lauren Cahn is a New York–based writer whose work has appeared regularly on Reader's Digest and in a variety of other publications since 2008. She covers life and style, popular culture, law, religion, health, fitness, yoga, entertaining and entertainment. Lauren is also an author of crime fiction, and her first full-length manuscript, "The Trust Game," was short-listed for the 2017 CLUE Award for emerging talent in the genre of suspense fiction.