Princess Di was always photographed by the paparazzi, not just for the drama she was at the center of, but also for her stunning and iconic outfits that the cameras captured wherever she went, even before she got married to Prince Charles. She was known for pushing boundaries with looks like sleeveless dresses, black outfits, and painted nails that all broke protocol. Here are her most inappropriate outfits.
1. Overalls
The Queen has always expressed her dislike of women in pants, so you can imagine how she felt when Diana wore pastel yellow overalls at Windsor Great Park for a polo match. She also wore wedged shoes to the match, which the Queen doesn’t like either.
2. A tuxedo
In 1984, Diana Spencer wore a tuxedo suit to a Genesis concert. It was groundbreaking and definitely broke all the rules, straying away from frilly styles as Diana started to define her looks with sleek, form-fitting designs. This goes to show that she paved the way for royal women like Meghan Markle to wear pantsuits. Now that’s what we call girl power!
3. A spaghetti strap red dress
In 1982, she wore a glittery chiffon gown designed by Bellville Sassoon to an event at Covent Garden. While the dress was stunning, it was a little revealing for Buckingham Palace and showed off quite a bit of shoulder for the time. This design would go on to create over 70 dresses for Diana.
4. An open-backed metallic dress
Diana skipped a modest gown and went for a dress that was considered very daring, as it bared her entire back. The dress, designed by Bruce Oldfield, broke a strict rule banning any backless dresses, which Diana boldly ignored.
5. Denim at a polo match
The princess wore light blue denim overalls to a polo match, pairing them with loafers and a white button-down shirt. Wearing a casual look was unheard of, as there were strict rules prohibiting denim and pants. Even to this day, royals like Kate Middleton wear pink luxury dresses and heels to polo matches.
6. Jeans and cowboy boots
Diana was a mom on the go, and her practical looks showed that. A popular outfit choice was a pair of cowboy boots paired with a baseball cap and jeans. She frequently wore this look to drop her kids off at school. She would also often wear sweatpants and a sweatshirt without any shame. Therefore, if you’re ever worried about rocking your old clothes, remember that Princess Di was never scared of it.
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.
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.
