Princess Diana’s Risque Ideas For Her ‘Famous Five’ Denied By Her Inner Circle

In the final years of her life, Princess Diana made bold statements, not just in her personal life, but also in fashion. After her separation from Prince Charles in 1992 and leading up to her untimely death in 1997, Diana took control of her public image in a way the world had never seen before. A key part of that transformation? The so-called “Famous Five” dresses designed by Jacques Azagury—daring, body-skimming creations that symbolized a woman reclaiming her power.

But according to Azagury, Diana wanted to go even further, and it was her inner circle that kept her risqué ideas in check.

Princess Diana’s ‘Famous Five’ Rewrote Royal Fashion Rules

From June 1995 to July 1997, Princess Diana stepped out in five boundary-pushing looks that would eventually be known as “The Famous Five.” Designed by Jacques Azagury, these dresses signaled a bold shift from the conservative styles she wore during her time as a working royal. Each look told a story—and together, they redefined Diana’s image in the public eye.

• The red Venice dress, worn in Italy in June 1995
• The black Bashir dress, worn twice—once in London and again in New York in 1995
• The blue Swan Lake dress, seen in June 1997 at a ballet performance
• The red Washington dress, worn during a U.S. visit on June 18, 1997
• The black birthday dress, worn on July 1, 1997—her final birthday and last red carpet appearance

Azagury, who worked closely with Diana for years, opened up on Hello!’s “A Right Royal Podcast” about the design process behind these looks. “She was always very excited by fashion,” he explained. “She knew she would please so many people just waiting for her to come out in the next dress.”

But not everyone was on board with Diana’s boldest ideas.

“We only disagreed when she wanted to go super short on the skirts,” Azagury said. “Paul Burrell, her butler, and myself would say, ‘That’s as short as you can go.’”

The Princess of Wales Wanted to Push Fashion Limits

While Diana may have wanted to take the plunge into even more revealing silhouettes, Azagury and Burrell served as the last line of defense—especially when it came to hemlines.

“Take the blue dress,” Azagury recalled. “She even wanted to go shorter than that. And we said, ‘There’s not much dress at the top, there’s not much dress at the bottom. You’ll end up with nothing in between.’”

Despite these creative negotiations, the dresses that did make it to the red carpet were enough to cement Diana’s status as a fashion icon and independent woman in charge of her own narrative.

“After the breakup of the marriage, she rediscovered herself,” Azagury told People. “She turned into this unbelievably stunning woman—not that she wasn’t before, but that’s when her personality really started to shine.”

He added that their time together was “just joyous,” and he never saw the “troubled Diana” the media loved to speculate about. “Every moment was so exciting to me, and we had so much fun.”

Tell us! What do you think of Princess Diana’s fashion choices following the end of her marriage to Prince Charles? Let us know in the comments below.

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