Princess Diana's Most Iconic Royal Rule-Breaking Outfits

Princess Diana spoke volumes through her fashion. When she was married to then-Prince Charles, her outfits reflected royal duty, but always with a dash of panache. She toed the line of dressing appropriately as the Princess of Wales, while simultaneously setting trends and inspiring women worldwide. But it was after her marriage to Charles ended — the two separated in December 1992 — that Diana's sartorial power really took shape. The infamous Christina Stambolian "revenge dress" set a precedent. On June 24, 1994, the day that Charles admitted on national TV to having an affair with Queen Camilla (known at the time as Camilla Parker-Bowles), Diana arrived at the Serpentine Gallery in London wearing a dress that did all the talking. "[Diana] didn't have to say anything with words," Deputy Style Director Brittany Talarico told People. "It was a fashion response — that dress became her clear message to Charles and the world." 

Arguably, Diana's style became even more interesting after her marriage ended. She wasn't stifled by royal protocol anymore and could dress as she pleased. Diana's hemlines shortened; her necklines dropped, and she sported a bare shoulder much more often than we ever saw in her days as a young bride. Because of this daring spirit, Dianacore still influences our contemporary fashion choices today. We look to her as an icon and trendsetter as she defied the rules that had previously been placed on her, and we can't help but celebrate that. Who doesn't love a rebel? 

One year after Princess Diana wore her imposing black "revenge dress," she attended another gala at the Serpentine Gallery, and wore something equally daring. In June 1995, Diana arrived at an event at the iconic London venue wearing a grey halter dress by fashion designer Catherine Walker. The dress had everything going for it: a plunging neckline, an exposed back, and a hem that cut off above the knee. Halter tops are certainly an unexpected sighting amongst royal women, and the sexier tone of Diana's outfit spoke to her shift away from the royal family towards a life of her own. 

We've seen something similar happen with her daughter-in-law; as Meghan Markle moved away from the royal family, both geographically and in terms of service, the actor has served her own style transformation. We think that Meghan was taking a page out of Diana's book, by letting the clothing speak for the wearer. It illustrates a deliberate choice to carve out one's own path. 

Long before celebrities of today experimented with the wet hair look, Princess Diana trailblazed that trend in grace and style. In January 1995, she traveled to New York to attend the Council of Fashion Designers of America Awards. She was there to present an award to her long-time friend and Editor-in-Chief of Harper's Bazaar, Elizabeth Tilberis, at Lincoln Center. For such a momentous occasion, Diana wore a long, navy dress by Catherine Walker with a criss-cross back design. She polished off the dramatic dress by wearing a pearl choker. 

In news clips from the time, Diana's presence at the CFDA Awards was a huge deal, and she overshadowed every other celebrity there. She was the big-ticket guest, and her gracious speech for Tilberis, along with her sensational look, truly delivered. There was something about Diana being in New York that gave her image that night a double removal from the royal roots she had left behind. She was across the pond, sporting slicked-back hair and a figure-hugging gown. By all accounts, she was the new Diana that night.

Princess Diana was a huge fan of Gianni Versace, and she wore the designer's masterpieces consistently. The sexy silhouettes and punchy colors favored by Versace suited Diana, particularly in her journey away from Buckingham Palace, as she pursued her own charities and ways of serving others. Versace saw that Diana was using clothing as a way to cut ties with her former husband and the royal family. "I had a fitting with her last week for new suits and clothing for spring, and she is so serene," Versace said of Diana in the July 1997 issue of Vanity Fair, (via Vogue.) "It is a moment in her life, I think, when she's found herself — the way she wants to live."

Versace shaped and supported Diana's evolution for years, and dressed her accordingly. At a charity concert in Italy in September 1995, where proceeds went to support Bosnian children, Diana wore a white, sleeveless Versace dress. While the simplicity of the color made the dress initially appear subtle, it was anything but. The scooped neckline brought with it a daring glamor, and the short cut of the dress was a seductive touch.  

Princess Diana knew the power of monochromatic dressing, and could make even a single tone look incredibly daring. At a ball for the Heart Foundation in Sydney, Australia in 1996, Diana again chose Versace to be her sartorial spokesman. She wore a dazzling blue, silk column dress that veered into one shoulder at the neckline, and kept the look tonal with a blue clutch and blue heels. The imposing outfit showed Diana in all of her power. She walked the red carpet alone and looked, dare we say, much more confident than when she walked carpets with then-Prince Charles. 

Diana's shift, both in terms of fashion and in terms of finding herself, has been evident to the people who've studied her style choices. Eleri Lynn, exhibition curator of "Diana: Her Fashion Story," told Marie Claire: "We see [Diana] growing in confidence throughout her life, increasingly taking control of how she was represented, and intelligently communicating through her clothes." While her daughter-in-law, Catherine, Princess of Wales, has remained in the royal family, we've seen a similar style transformation in her. Both women hit really interesting periods in their 30s where they were able to curate looks that spoke to their particular places in life. While Catherine is arguably more conservative than her late mother-in-law, the same independent spirit shines through. 

On June 3, 1997, Princess Diana attended a performance of "Swan Lake" in London. For the big night out, Diana wore what seemed to become her post-royal silhouette: a mini dress with thick straps and a scooped neckline. It's no wonder this cut became one of her favorites because it was so flattering on her. That night, she wore a glittering, baby blue mini dress and paired it with silver heels. She also rocked the quintessential Diana manicure: a classic, French tip. On top of that, she wore some unbelievably decadent jewelry that complemented the glitzy dress. It was the ultimate expression of Diana's confident, personal style.

Diana's pearl and diamond necklace, suitably dubbed the "Swan Lake" necklace, was up for auction in 2017 and expected to sell for $12 million. It ended up being privately sold to a museum. The necklace was made by royal jeweller, Garrard, and was supposed to come with matching earrings that weren't finished in time for her night out. Sadly, Diana never got to wear the earrings because she died tragically later that summer. Her trip to "Swan Lake" was one of Diana's last public appearances.