Princess Diana Looks That The Queen Didn’t Approve Of

Published on June 5, 2019. Updated September 5, 2019

When Lady Diana Spencer joined the royal family she revolutionized previous royal traditions and brought a fresh, hands-on approach to being a public figure. She broke down the barriers of stuffy, outdated royal conventions and made the entire institution much more personal with her humble and compassionate ways. One of the most apparent traditions Diana broke was when it came to fashion! She breathed new life into royal dressing and added her own trendy twist to her outfits while still looking dignified and presentable. Although we love Diana’s propensity for bold style, it was quite shocking at the time and many of her statement looks definitely got a second glance or two for breaking royal style rules. Follow along for 20 of Princess Diana’s most controversial looks:

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20. Low Back

Diana was known for forging her own path when it came to fashion and many of her outfits broke traditional style rules that were expected of Royal women. One, in particular, is this crushed velvet dress she wore to meet ballet dancers at Saddlers Wells theatre. The look was a gorgeous burgundy color and featured an oversized bow on the back. The real standout with this look, however, is the super low back that we’re quite certain the Queen wouldn’t have approved.

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19. Wedding Look

Princess Diana’s wedding dress was certainly a product of its time. The ’80s were huge on extravagant, over the top wedding gowns, which is exactly what Princess Diana’s was with the oversized sleeves and voluminous skirt. While it’s true that the Queen must approve the Royal wedding gown before it is debuted, we imagine she might have had mixed opinions about the grandiosity of Diana’s look considering the Queen’s own wedding gown was much more simple and sleek.

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18. Low Neckline

Low necklines and royalty rarely go hand-in-hand! The royal family is known for being quite modest and conservative in the fashion department, which is why we can’t imagine the Queen would have approved some of Diana’s more lowcut numbers, like this look she wore to a Charity Dinner At The New York Hilton Hotel.

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17. Wedges

The Queen has publically expressed her dislike of wedge-style shoes, so we can almost guarantee she scoffed at this casual look worn by Princess Diana in July 1981. Not only did the casual look involve overalls, but it also showcased bright pink wedges peaking out from beneath her pants.

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16. Bike shorts

Bike shorts were one of Princess Diana’s go-to looks during her casual off-duty days in the ’90s. While we love seeing Diana in her comfortable, relaxed outfits, we’re not sure the Queen would say the same, especially for shorts this tiny and short!

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15. Sheer Skirt

This photo of Princess Diana is one of the most iconic of all time from when she was first dating Prince Charles and working as a Kindergarten assistant. The sunlight in this photo made the skirt appear sheer which displayed a silhouette of her legs. We’re certain that once she married into the Royal family that the Queen took precautions to help Diana have a more suitable and less revealing Royal wardrobe.

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14. Engagement Look

One of Princess Diana’s most controversial looks was actually the azure blue set that she wore to publically announce her engagement to Prince Charles at Buckingham Palace. Allegedly Diana pulled the ensemble from the racks of Harrods department store last minute, which was a surprise to many! She supposedly attempted to visit the high-end boutique Belville Sassoon but was advised by the French sales assistant, whom obviously didn’t recognize Diana at the time, to visit a more budget-friendly store. Once the mishap was realized, Diana was welcomed back to their boutique which initiated the beginning of a long-time fashion partnership.

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13. Oversized tailoring

One of Diana’s go-to styles was oversized blazers and tailoring. The Princess obviously had quite the penchant for style and predicting trends because nowadays these styles are seeping back into the mainstream decades later. At the time, however, a Princess wearing anything oversized or not perfectly fitted to her body was quite controversial and something that hadn’t been done before.

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12. Revenge Dress

One of Princess Diana’s most iconic outfits is undeniably this off-the-shoulder minidress which was dubbed the “revenge dress” since she stepped out in it just following Prince Charles’ televised confession of infidelity. The revealing, leggy number was the perfect choice for a power outfit and Diana definitely had all eyes on her for more reasons than just Charles’ affair that evening at the Serpentine Gallery benefit. The dress was more revealing than her previous royal looks, but with her newfound freedom came a newfound love for even bolder fashion.

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11. No hat

It was often expected for British royals to wear hats and fascinators for public outings, but Diana didn’t always abide by this rule! According to British Vogue, Diana was very intentional with her clothing and thought about the perception each piece would give off. Hats, for example, she thought made her seem unapproachable and even explicitly stated, “You can’t cuddle a child in a hat.” Although she did wear hats on most formal occasions, for hospital visits or visiting children, she refused to abide by this royal fashion protocol.

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10. All black

It was often expected that royals standout when they attend royal outings, with Queen Elizabeth setting the standard with her brightly colored suits in every shade of the rainbow. Allegedly the Queen opts for these colors to ensure members of the public are able to see her amongst a crowd and are able to say “I saw the Queen!” Diana, however, didn’t follow this practice and had an obvious fashion propensity for black, navy and neutrals.

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9. No gloves

Similar to her no hat policy, Diana reverted the previous royal tradition to wear gloves for public outings! Instead, she opted to keep her hands bare to allow a personal touch and skin-to-skin contact with those she met. Previously, it was expected that royals were higher in the social hierarchy and should not be touched, but Diana changed these notions with her humble demeanor and down-to-earth way of royal life.

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8. One-shoulder neckline

The royal family never typically opted for anything overly fashion-forward or revealing, until Princess Diana joined the family, that is! Diana loved fashion and took to trendy cuts and styles when it came to dresses, such as this one-shoulder neckline. Nothing like this had ever been worn by a royal before, and it was quite refreshing to see a royal chose something sparkling and on-trend rather than something rather dull and lackluster.

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7. Wore necklace as a tiara

Diana loved to style her clothes in new and interesting ways and this look from a gala in Australia is the perfect example of that! The sparkling headpiece Diana wore was actually a necklace that was gifted to her by the Queen. It was remodeled for Queen Mary, then inherited by Queen Elizabeth in 1953, who chose to pass it down to Diana as a wedding gift. We’re quite certain this isn’t the way the Queen had in mind for Diana to style the piece, but we love her unique take on the traditional emerald necklace!

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6. Casual fashion

Diana gave a new meaning to casual fashion when she joined the royal family! Before her, it was rare to see a royal wearing anything remotely informal, but Diana’s down-to-earth personality definitely gave way to a more low key style uniform within the royal family. This particular outfit was definitely one of her most casual consisting of a reindeer-printed knit sweater layered on top of a turtleneck and loose-fitting corduroy pants.

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5. Chunky jewelry

Before Diana, it was common practice for royals to be quite minimalist in nature when it came to jewelry. They had their statement tiaras and family heirlooms but tended to wear only one to avoid looking overly glamorous or flashy. Diana, however, had a penchant for wearing chunky, oversized jewelry and did so with pride. This sapphire choker, for example, was one of her go-to pieces and she had no problem styling it with dangling earrings or a sparkly, pearl dress.

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4. Flashy textures

Royals definitely want to stand out when they attend an event, but Diana took this to the next level with her textured, glittering outfits! She loved flashy sparkles and embellishment, and sometimes both. This particular look consisted of a sleek dress that was covered in head to toe pearls which she paired with a suit jacket that matched perfectly with the dress.

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3. Short shorts

Just when we thought Diana’s reindeer-printed sweater was super casual, she later stepped out wearing this shorts and tank top combo that definitely topped it! It’s rare to see a royal wearing something as mainstream as short shorts but we love her fresh take on royal fashion. The look is a timeless vacation style and definitely quite practical for the sweltering summer heat.

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2. Sheer paneling

By now, it’s quite clear that Diana wasn’t afraid to show a little skin despite being part of the royal family. This particular gala look was definitely one of her most controversial. The crisp white outfit consisted of sheer paneling along the chest that many found quite shocking for a member of the royal family and something more suited for a celebrity or actress.

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1. Knee-baring

One of the Queen’s biggest style rules is to never show your knees during a formal public appearance. Kate Middleton has broken this rule a few times, but for the most part, she stays relatively modest with her skirt lengths. Diana, however, loved to show a little leg, and she definitely had the figure to do it! Mid-thigh dresses looked absolutely fabulous on the royal, despite how controversial these looks may have been at the time.

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