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? 

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 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.