The Revealing Outfit That Had Princess Diana Second-Guessing Her Look

The Met Gala is a mecca for fashion royalty today, but in 1996, the prestigious New York City event hosted a real royal in Princess Diana. The Princess of Wales wowed fans, paparazzi, and fellow attendees when she arrived on the exclusive red carpet that December — the Met Gala wasn't always on the first Monday in May! — and it wasn't just because of her title. Her divorce from then-Prince Charles finalized, Diana was in a lucrative position: no longer bound by strict royal rules, but still immersed in the star power of the palace. Using her newfound freedom to her advantage, she opted for a slinky 'fit that likely wouldn't have surfaced in her early-'80s wardrobe. 

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At the Met Gala, the fashion event of the year, Diana rocked a silk number by John Galliano for Dior. She still dazzled with her elegant sapphire and diamond jewelry, along with her iconic Lady Dior bag, but the dress itself was unique for her, being trimmed in lace. Together with the silk and lower neckline, the slip was giving lingerie — a far cry from the more whimsical, romantic style the princess had sported more than a decade earlier, when she first came to the world's attention. 

Writing for the Daily Mail, Vogue fashion critic Sarah Mower revealed that she'd spoken to the editor of Harper's Bazaar at the time, Liz Tilberis, who invited and accompanied Diana that night. Tilberis shared that Diana was "a bit iffy about the cut of the dress" and was concerned Prince William wouldn't like it because it was "so bare." William has never commented on his mother's Met Gala dress, but whatever concerns Diana had, she seemingly got over them quickly, moving toward increasingly boundary-pushing fashion in 1997.

Princess Diana's fashion changed remarkably after she left the royal family. Though her separation from Prince Charles came as early as 1993, the two weren't officially divorced until 1996. In that time, the princess increasingly gravitated toward more surprising pieces, including non-British designers and bolder styles. According to designer Jacques Azagury, who worked with the princess, she wanted shorter hemlines than even her advisors and stylists would allow.

"Paul Burrell, her butler, and myself would say, 'That's as short as you can go,'" Azagury revealed on Hello! Magazine's "A Right Royal Podcast." The designer added, "Take the blue dress [which she wore to attend 'Swan Lake' in 1997]. She even wanted to go shorter than that on the dress. And we said, 'Well, look, there's not much dress at the top, there's not much dress at the bottom. You'll end up with nothing in between." Azagury further explained that while Diana's marriage breakup must have been heartbreaking, it did lead to a new beginning as far as her fashion was concerned: "... she rediscovered herself and she turned into this unbelievably stunning woman — not that she wasn't before, but that's when her personality really started to shine."

Throughout 1997, Diana constantly reached for tank dresses that tended to show more cleavage than her earlier dresses did, and according to these claims, they may have been even shorter if she'd gotten her way. During this period, Princess Diana utilized her street style to send a message to the royal family and the world: She was a free agent in charge of her own style, and she was going to embrace her star power rather than hide it away. Case in point? Check out Princess Diana's leggiest looks after leaving the royal family.