She will forever be the people’s princess. The late Princess Diana was truly an influential figure known all over the world for her natural empathy and rule-breaking confidence. After joining the royal family at just 19 years old upon marrying ex-husband Prince Charles, Diana became a fan-favorite icon for her stunning smile and fashion statements, with some of them even considered to be daring outfits for a modest royal. 

Perhaps one of her most significant style choices was her 1994 black mini V-neck gown, known as the “revenge dress.” The Princess of Wales stepped out wearing the bold ensemble shortly after news broke of the Prince of Wales’ affair with now-wife and Duchess of Cornwall, Camilla Parker Bowles

The simple yet bold dress fit right above her knees and featured a subtle chiffon train in the back. Diana also wore matching black heels as she confidently shook hands at the Vanity Fair London party that year. 

On another occasion, she danced the night away with actor John Travolta at a White House dinner in 1985, effortlessly twirling in a sexy and chic black ballgown. She also completed the outfit with a classy pearl necklace encrusted with a black oval center. 

Sometimes, however, Diana would choose to go casual in jeans and sneakers throughout the 1990s. As a devoted mother to her sons, Prince William and Prince Harry, Diana was even seen taking them out on fun mother-son outings, such as visiting amusement parks and going on fast-food runs from time to time. 

Whenever she visited children in other countries or in the U.K., the late Princess of Wales considered what to wear for these specific occasions, usually opting for her blue floral dress. 

“She called it her caring dress,” Matthew Storey, fashion curator for Royal Style in the Making, previously told Us Weekly. “It’s this blue dress with bright flowers on it and it was one of the princess’ favorite dresses. She wore it over and over again. So much so that the press said, ‘Give it a rest. Stop wearing it.”

Despite having worn it several times, Diana still knew it was the best decision because she “knew that children really responded to this dress,” Matthew added. 

“Children love bright colors,” he continued. “So, she often wore it when she was going to visit children — and sick children in particular.” 

Scroll through the gallery to look back at the late princess’ most daring outfits. 


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Tyler Cowan