Princess Diana’s Naughtiest Outfits Revealed 》

Princess Diana is generally remembered for two things: her messy divorce from King Charles and her service to others, the latter of which earned her the nickname “The People’s Princess.” Even as she continued to fall out of favor with the Royal Family, her popularity soared throughout the world.

Of course, part of what made Diana so popular was her beauty. In addition to her naturally beautiful features, the princess dressed to impress and wasn’t afraid to ruffle some feathers. Accordingly, she wore some downright naughty outfits that have only gained more attention over time.

Just what were Diana’s naughtiest outfits? Keep reading to discover the most risque looks she unleashed on the world!

Divorced Diana dresses to impress

While she still took some major fashion risks while married (more on this later), most of Princess Diana’s naughtiest outfits debuted after her divorce from Charles. This includes the midnight blue slip dress she wore to the 1996 Met Gala. It might not seem scandalous in this modern age, but everything from the slender shoulder straps to the black lace trim made the dress seem downright provocative.

Some pundits compared her killer dress to sexy evening wear, and Diana hesitated to wear it that evening. She wasn’t worried about what the press would say, though…she was more concerned with what the teenage Prince William thought. She didn’t want to embarrass the young lad, but with his apparent approval, Diana had the dress made to be even more revealing than before.

The final result, of course, was nothing short of fabulous.

Princess Diana busts out

It’s fair to say that Diana dazzled us with her fashion choices from almost the beginning of her relationship with Charles. In 1981, for example, she went with him to a concert at Goldsmith’s Hall. This was their first official outing since getting engaged, and the eyes of the world were on Diana that night.

Instead of wearing something very conservative, though, Diana wore a dark frock that she had longed for ever since seeing it on display. The strapless nature of the frock made it seem very provocative for the time period, but what really stood out (quite literally) with this dress was how it emphasized Diana’s breasts. She was practically spilling out of the frock, and she quickly discovered that bending over when she got out of a car showed the world a little too much than intended.

That didn’t stop Diana from dressing provocatively. Later on, she fixed the problem by utilizing special “cleavage bags” meant to hide her breasts as she got out of vehicles!

Leggy in her athleisure

Most of the naughty Princess Diana outfits on this list are elaborate and expensive dresses. After all, what else would you expect from someone who married into one of the wealthiest families in the world? However, Diana once became both a scandal and a sensation for the most lo-fi fashion of them all: athleisure wear. She was a connoisseur of this overlooked fashion art and created some killer looks that many are still trying to emulate to this day.

For instance, in this photo, she paired bike shorts with a big sweater. For a royal like Diana, this was probably the equivalent of most of us throwing on a ratty pair of old jeans to go check the mail. But she quickly made it her signature look, wearing it repeatedly in hopes of foiling paparazzi who wanted to see her in a new outfit.

Strictly speaking, those short shorts violate royal fashion protocol. But you don’t exactly become an icon by following the rules, do you?

Showing crazy cleavage

Early on, Princess Diana had to make a very important fashion choice. She could start dressing more conservatively, which would allow her to stop worrying about accidentally giving the paparazzi a show. Or she could figure out a way to solve that particular problem and still dress as provocatively as she wanted. To our surprise and delight, she chose the latter option!

Diana is so busty in this dress that she had to use one of those aforementioned “cleavage bags,” a nickname she gave to her special clutches designed to disguise her décolletage when she got out of the car. In this case, one of those bags helped protect her modesty when she got out of the car at Royal Albert Hall in 1997 while wearing a delicious blue mini dress.

With looks like this, who can keep their eyes on the ballet?

The infamous ‘revenge dress’

You’ve probably heard the phrase “the best revenge is good living.” That wasn’t really the case for Diana, though. After her messy divorce from Charles, she decided the best revenge was dressing to the nines and showing the prince (not to mention the world) exactly what he was missing out on.

She had been invited to a Vanity Fair soiree at the Serpentine Gallery, and she showed up dressed to kill in history’s most famous little black dress. Even though she had owned the dress for years, a narrative quickly emerged that this was her “revenge dress,” one that showed off her great beauty and sent a not-so-subtle message to her ex-husband that she wouldn’t quietly fade away from the public eye now that she was free of him.

All these years later, we can’t get over how sexy she looked in this dress. Revenge has never felt–or looked–better!