Celebrity Style

15 Times Princess Diana Styled Headwear To Perfection

And her tiara hacks were stellar.

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Princess Diana's hats, tiaras, and baseball caps were always styled to perfection.
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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 gusto.

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, 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: To give the illusion that the tiara was 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 the headwear to hide the structural metal and clips.

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 15.

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 and handed down to Queen Elizabeth II before making its way to Princess Diana. 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 headpiece.

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 and matched her gown 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 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 portion of her 22nd birthday celebration in 1983, Diana went all out with her headwear.

Slipping into a navy blue and pink polka-dot silk dress and pink coat, she chose a deep navy hue for her wide-brimmed wool hat. It 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 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 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 in 1997 — until 2018, when her niece, Celia McCorquodale, wore it for her wedding to George Woodhouse.

Princess Diana’s Black Tam O’ Shanter Hat

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For their first public appearance after their wedding a few months prior, Princess Diana and Prince Charles attended the September 5, 1981 Highland Games in Braemar, Scotland. Dressed for the occasion, Princess Diana was clad in a button-up long-sleeved tartan dress and an equally fitting black tam o’ shanter flat bonnet hat.

Princess Diana’s Ret Brimmed Hat

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One of the royal family holiday traditions is to spend Christmas at the Sandringham House in Norfolk, England. During the holidays in 1990, Princess Diana sported her iconic two-piece houndstooth outfit, complete with a black and white skirt, a red and white jacket, and a wide-brimmed red hat with a mini veil.

Princess Diana’s Military Uniform

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Before Princess Diana’s second son, Prince Harry, began his own training at the Sandhurst Royal Military Academy, she attended the Passing Out Parade at the academy on April 10, 1987. She wore a military-inspired suit by Catherine Walker and a matching hat by Graham Smith for the occasion.

Princess Diana’s Netted Visor Hat

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On November 12, 1990, Princess Diana attended former Japanese Emperor Akihito’s enthronement ceremony at the Imperial Palace in Tokyo. She dressed in all white with a smart structured jacket and pearls — but the real kicker was her lavish netted visor.

Princess Diana’s Frederick Fox Wine Hat

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On April 28, 1985, Princess Diana and Prince Charles paid a visit to the Anzio Beach Head War Cemetery in Italy to honor the lives lost in the Allied landings in 1944. Princess Diana wore a striped wine-colored dress by Catherine Walker and a positively sophisticated matching hat by Frederick Fox.

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