Princess Diana Looks That Had Deeper Meaning Than You Knew

Although Princess Diana wasn't immediately considered a fashion icon — her engagement photo outfit was considered frumpy even by 1981 standards — she eventually came into her own. As she matured and realized the impact she was having on not just the U.K. but the world as a whole, Diana learned to dress the part of royalty. Then, when her marriage was over, Diana's post-Charles looks further solidified her as a style icon, as well as someone ready to shed her past and move forward into a new chapter in her life.

"What Diana did when she came onto the scene in the early ['80s was that] she made [royal fashion] exciting," journalist and royal fashion expert Elizabeth Holmes told Fashion in 2022. As Holmes explained, Diana did this by opting for trending pieces and bold colors. "She understood not just how clothing looked, but how it felt to wear a fantastic dress, and how it made the viewer feel," Holmes said.

Not only did Diana know that clothing could be a way to connect to those watching her every move, but she also used it to speak her mind and communicate her feelings, breaking royal fashion rules along the way. In other words, there was no accident in what (and when) Princess Diana chose to wear. Whether you're simply a fan of the royals or committed to the fashion aesthetic Dianacore, Princess Diana is the only inspiration you need.

When it comes to the concept of the revenge dress, we have Princess Diana to thank. In June 1994, after Prince Charles went public with his infidelity, Diana attended the Serpentine Gallery in London, rocking a little black dress by Christina Stambolian. Just above the knee and falling off the shoulder with a sweetheart neckline, this body-hugging dress spoke volumes. Not only was Diana officially free of Charles and the royal family, but she proved that she had survived her heartache and came out the other side. While there's a long list of celebrity revenge dress moments we'll never forget, no one has ever made revenge look as good as Princess Diana.

When Princess Diana attended the Cannes Film Festival in 1987, she chose to pay homage to Princess Grace of Monaco with a stunning light blue chiffon gown and matching scarf by Catherine Walker. While not an exact dupe of the gown that Grace Kelly wore in 1955's "To Catch A Thief," it was a beautiful, modern take on the original. And considering it was filmed in the French Riviera, it was a perfect choice. Early in her relationship with Charles, Diana had sought advice from Grace Kelly on navigating becoming part of a royal family, to which Kelly offered, "Don't worry, dear. You see, it'll only get worse," according to "Diana: Her True Story."

It's not often that you see a 25-foot-long train on a wedding dress, but that's exactly what the world saw when Princess Diana married Charles in July 1981. It's also not every day that a bride of such international fame chooses designers who just graduated from the Royal College of Art. "It was all about drama and making Diana a fairytale princess," designer Elizabeth Emanuel told British Vogue in 2020, adding that its creation felt like an extension of their final show that they'd done for fashion school. "Diana was still developing her sense of style at the time ... She left it to us and our brand of new-romanticism," Emanuel said of herself and her then-partner David. Naturally, the designers' careers skyrocketed after that.

In a true "Pretty Woman" moment, Princess Diana was initially turned away from the shop where she purchased her honeymoon ensemble. It turns out that in trying to find the right look for her engagement photos, Diana popped into Bellville Sassoon and, instead of helping her find something, the associate suggested she go to Harrods. "You can imagine how Belinda [Bellville] and David [Sassoon] felt when they realized the future Princess of Wales had been turned away," curator of the Royal Style in Making exhibit, Matthew Storey, told People in June 2021. Luckily, Diana returned to the boutique with her mother, was taken more seriously, and found something for the engagement photos. Bellville Sassoon also custom-designed Diana's honeymoon look.

Of all the looks Princess Diana wore, the Rowing Blazers red sweater with the single black sheep amongst all the white ones truly speaks volumes. She wore this sweater to one of Charles' polo matches in 1981 when she was only 19 years old, and she and Charles had already been engaged for four months. Because it was assumed that all was well and the two were in love, it wouldn't be until later that the sweater was seen as an allegory for how Diana saw herself within the royal family. After all, Diana met Princess Grace for the first time in March of that year, and she had already, in her own way, told the young princess to buckle up for the ride ahead.

Although not officially divorced at the time, Princess Diana had been separated from Charles for quite a while when she rocked a white Versace mini dress in 1995 while in Milan attending a charity event. With this dress, Diana said a lot about who she was and the direction she wanted to go since being freed from royal decorum. Just a month before her death, Diana graced the July 1997 issue of "Vanity Fair." In the accompanying article, Gianni Versace said of Diana, "I had a fitting with her last week for new suits and clothing for spring, and she is so serene. It is a moment in her life, I think, when she's found herself — the way she wants to live" (via British Vogue).

Despite the fact that Princess Diana had been on the global stage since her 1981 marriage to Charles, she only attended the Met Gala once in 1996. That year, the theme was simply Christian Dior, and John Galliano famously designed a custom full-length slip dress for the princess. Throughout the 1990s, slip dresses — which recently had a comeback in 2023 — were everywhere, and some of them were quite revealing. According to a 2018 interview with the Wall Street Journal (WSJ), Galliano said it was Diana's idea to remove the interior bustier, therefore going braless, upping the provocative factor. 'It was a reflection of how she was already feeling: liberated," Galliano told WSJ.

Princess Diana had a glorious love affair with the color pink and wore every possible shade throughout her life, proving that such a feminine color could also be statement-making and empowering. Of all the pink outfits Diana wore, it was her Versace suit with matching pillbox hat by Philip Sommerville that she sported for a visit to Howe Barracks in 1995 that remains unforgettable. Not only because she's clearly channeling another fashion icon, Jackie O., with her clean lines, sophisticated set, and pillbox hat, but because she took back her power in a color she loved and in a design that was the pure embodiment of strength.

This photo is particularly heartbreaking because it was taken less than two months before Princess Diana would die in a car accident, but there is something uplifting about it, too; she looks at peace, and she's having fun. Taken on July 17, 1994, which was also Camilla Bowles' birthday, celebrated at a party thrown by Charles, there's a lot to be interpreted here. As royal commentator Richard Fitzwilliams told Time via InStyle, the two were in public competition, and that led to Diana making sure she was spotted in her bathing suits as much as possible while vacationing in St. Tropez. Sometimes, swimwear is just swimwear, while other times it's a middle finger to the person who broke your heart.