7. A one-shouldered dress
In 1991, she wore a Catherine Walker gown on a trip to Brazil. The dress had a column silhouette with a one-shoulder neckline, and many have dubbed it one of the most historically daring outfits ever worn by a royal, as one of her shoulders was fully exposed (which is a big deal to the royals, if you couldn’t tell by now).
8. Wearing a choker as a tiara
Ever the trendsetter, Diana rewrote the rules when she repurposed the royal family’s jewelry from its traditional intent. She was photographed wearing a choker as a headband, and while you might not think wearing a piece of jewelry in a new way is a big deal, it broke rules; you’re not meant to wear a tiara till your wedding day, and not meant to wear diamonds during the daytime.ё
9. The famous revenge dress
If there’s one dress we’ll always remember Princess Di in, it’s when she shows up at the Serpentine Gallery gala in 1994 in a tight black chiffon dress that was cut above the knees, with black stockings and pumps. It was a sexy, sleek look, and she wore it on the same day that Prince Charles admitted on national TV that he had been cheating on her. Her appearance was striking, clearly intended to send a strong message to Prince Charles!
10. Tight biker shorts
Royal women aren’t supposed to show off their skin, and wearing booty-hugging bike shorts with messy hair was definitely against protocol. We can’t blame her—much of the time she wore these shorts, she was leaving the gym, but it was still considered inappropriate, even after her divorce.
