Celebrity Style

10 Times Princess Diana Styled Headwear To Perfection

And her tiara hacks were stellar.

Princess Diana's hats, tiaras, and baseball caps were always styled to perfection, and she had a gen...
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When it comes to Princess Diana’s style, she loved to invest in a memorable look from head to toe. And yes, that included headwear. Be it a hat, fascinator, headband, or, for Princess Diana, a tiara, she was rarely seen without a topper finishing off her look like only she could. Silk hats for evening events? Chokers worn as headbands? There was no headwear trend Princess Diana didn’t embrace with style.

Though hats were her most-often-worn type of headwear, her pieces ran the gamut from baseball caps to wide-brimmed numbers, cloches to berets. For official royal evening affairs, however, tiaras were nearly always on the menu, and the young royal had quite the style hack for making sure she looked as pristine as possible.

In order to make it seem as though all of her tiaras were practically floating effortlessly in her hair, she used more than just an army of bobby pins. Princess Diana would wrap yellow ribbon around the base of her tiara to hide the structural metal and clips in the most discreet way possible. Genius!

While Princess Diana’s overall style was definitely iconic, one must never forget about the finishing touches that were her headpieces. Ahead, find the top 10.

Princess Diana’s Lover’s Knot Tiara

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The Lover’s Knot Tiara was designed by Crown Jeweler Garrard, and it was widely noted to be the favorite of Lady Di’s collection. Even so, rumor has it that it was one of the heavier of the bunch and it often gave her a headache when she wore it for extended periods of time.

It was commissioned in 1913 by Queen Mary, copying the Cambridge Lover’s Knot Tiara, which belonged to her aunt, the Grand Duchess of Mecklenburg-Strelitz. The tiara features round-cut diamonds that make up a scalloped frame, with 19 hanging drop pearls nestled within each opening.

Though the tiara was a gift, it was bestowed to the Princess of Wales and not to Diana Spencer, which meant that when she and Prince Charles got divorced, Princess Diana was required to give up her rights to the epic head piece.

Princess Diana’s Choker Worn As A Headband

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Princess Diana was well known for repurposing jewelry, most iconically by wearing chokers as headbands.

At a gala dinner in Melbourne, Australia in 1985, Diana chose an art deco emerald and diamond choker that had once belonged to Queen Mary to style in her hair. Matching her gown nearly perfectly, she fastened the jewels to her forehead, nestled in her blonde ’do.

Princess Diana’s Red Cloche

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At the Aintree racecourse for the Grand National in 1982, Diana chose to top her red and blue look with a matching deep red hat. The style chosen was a variation on the cloche style, with a short brim, though the Princess’ version tipped up to one side, revealing a twisted fabric fitting underneath.

Princess Diana’s Beret

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One of the huge trends of the 1980s was the beret, and Princess Diana wore it with ease. In 1984, she boarded the Royal Princess cruise ship, named after her, wearing a bright red pencil skirt suit and black accessories. Her hat matched her perfectly, in the same bright red color with a black velvet edge.

Princess Diana’s Feathered Hat

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Why just wear a hat when you can add a giant feather to your look? For the daytime celebration in 1983 for her 22nd birthday, Diana went all out with her headwear.

Slipping into a navy blue-and-pink polka-dot silk dress and pink coat on top, she chose a deep navy hue for her wide-brimmed wool hat that was adorned with a matching feather to give it that little something extra.

Princess Diana’s Green And White Hat

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In 1988 for the Trooping the Colour, Princess Diana not only matched her hat to her clothing, but also to the wardrobe of her youngest son, Prince Harry.

Diana chose an emerald green and white dress that matched Harry’s shorts and suspenders. On her head was a giant brimmed, round-top hat in the same shade of green with a light-catching white trim.

Princess Diana’s Fascinator

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In 1983, Princess Diana was photographed in one of her most iconic looks while on a royal visit to Australia. For one of the events during her stay, she donned a pink-and-white polka-dot silk dress from Donald Campbell that she paired with a coordinated pink fascinator.

Boasting a giant silk bow to the right side, the hat was designed by John Boyd, a hat maker with whom Diana had a long and consistent design relationship.

Princess Diana’s Baseball Cap

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Diana might have stunned in many a cocktail dress or ballgown, but she could hang with the best of the casual dressers as well. At Guards Polo Club in 1988 with Prince William, Diana topped her denim and sweatshirt look with a classic navy baseball cap.

Princess Diana’s Colorful Silk Hat

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For the Governor’s Launch in 1989, Diana slipped into a red and purple silk suit designed by Catherine Walker. With it, she sported a wide-brimmed purple and red silk hat that proved that hats could be worn every moment of the day with ease.

Princess Diana’s Spencer Tiara

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In addition to Princess Diana’s many royal jewels, she also possessed a collection of baubles from her family. One such piece was the Spencer Tiara, which was not only her wedding day choice, but one that she wore most often after that as well.

Mounted in gold, the Spencer Tiara boasts stylized flowers and scrolls that are crafted of silver-set diamonds.

This tiara was also worn by both of her sisters, Lady Sarah and Lady Jane, as well as her sister-in-law, Victoria Lockwood, on their wedding days. Now belonging to her brother, Charles Spencer, the tiara had not been seen publicly since her passing away in 1997 until 2018 when her niece, Celia McCorquodale, wore it for her wedding to George Woodhouse.