Princess Diana's Most Inappropriate Outfits

Throughout her life in the limelight, Princess Diana Spencer was consistently photographed. Whether she was attending a polo match with Prince Charles, taking her sons to school, attending a formal event, or visiting with organizations, she was almost always the center of attention.

Spencer attracted the paparazzi and the cameras early on in her life as a royal. Even before her marriage to Prince Charles, she amassed such innate interest — to put it plainly, people were just obsessed with her. As such, the cameras followed her everywhere and captured just about everything she did and, as a result, froze her most iconic outfit options in time.

The princess' outfit options were often a heightened point of interest, as she pushed the envelope unlike any other royal before her. She wore black, painted her nails, opted for sleeveless dresses, and did not shy away from the bold and memorable. But due to her choices, some of her outfits were seen as highly inappropriate (and many broke royal dress protocol). So with heightened interest in her life and everything she chose to wear, here are Princess Diana's most inappropriate outfits.

Princess Diana Spencer broke the rules from the beginning, and we love her all the more for it. As noted by PopSugar, Spencer chose a pair of pastel yellow overalls and a coordinated top for a polo match at Windsor Great Park. She finished the look with a pair of wedges and left a pair of sunglasses perched on her head (exactly where her tiaras would be placed). It was just a pair of overalls, so what was the big deal? Well the outfit broke a number of royal dress protocols. 

As noted by Cosmopolitan, the queen prefers dresses and skirts over trousers and has made that perfectly clear to the royal ladies who have followed in Spencer's footsteps (think Kate Middleton and Meghan Markle). Cosmopolitan also reported that Queen Elizabeth II is not a fan of wedges and has pointed that out to the royal ladies. "The Queen isn't a fan of wedged shoes," a source told Vanity Fair. "She really doesn't like them and it's well known among the women in the family." Looks like Princess Diana broke all the rules before she even became a royal herself.

When people think of the royal women, it should come as no surprise that they picture femininity, elegance, and sparkly crowns. But Princess Diana Spencer did not concede to such limited perspectives on what she could be or what she could wear, and she made that perfectly clear in 1984. 

As noted by the Daily Mail, she chose to wear a tuxedo suit while attending a Genesis concert. The look was as inappropriate for a royal as it was groundbreaking, and it served as a turning point for Diana's sense of style. The Daily Mail reported that by the time of the mid-1980s, she transitioned from frilly dresses with a lot of volume to sleek, form-fitting designs that were as body conscious as they were defiant of royal expectations. 

Diana clearly paved the way for royal women to rock a pantsuit because Meghan Markle has been spotted on occasion in similar ensembles. As noted by Cosmopolitan, Markle wore a Givenchy blazer and trouser combo while on a trip to Ireland, and has made several formal appearances in pants. Take that, royal protocol.

Princess Diana Spencer really stunned from the start of her royal career, but just because her outfits were head-turning, that doesn't mean that the royal precedent was being honored. While attending an event at Covent Garden in 1982, she opted for a glittery chiffon gown by designer Bellville Sassoon (via the Daily Mail), and while she looked beautiful, her choice defied expectations and broke dress protocol. 

The royal precedent, until Diana's time, was often made up of the royal women covering up — modesty was always a good option. Instead of conforming, she shocked the system with her spaghetti strap gown, showing every inch of shoulder she had while attending the event. As noted by the Daily Mail, Sassoon continued to serve as a favorite designer of hers, and went on to create more than 70 dresses for her over a two-decade time period — clearly, he had an inkling as to what she was trying to accomplish with her look. 

But the modest royal protocol still stands, and royals like Meghan Markle have been brutally criticized for showing too much skin.

Talk about pushing the boundaries as far as they will go — while in Melbourne in 1985, Princess Diana Spencer did not go for the traditional pencil skirt or the modest ball gown, but instead opted for a backless metallic dress that was as daring as it was inappropriate. As noted by the Daily Mail, her dress was by designer Bruce Oldfield and featured a very 1980s look — if metallic and shoulder pads doesn't say '80s, then what does? 

But clearly the members of the royal institution were not fans of Diana's look, and strict dress codes were put in place for royal events such as the Royal Ascot. As noted by the Daily Mail in 2012, new fashion rules were put in place that prevented any backless dresses, bare shoulders, and short hemlines. "Hats with a diameter of four inches or more are mandatory," the Daily Mail reported. "Skirts must sit no higher than just above the knee, and dresses that are strapless, off the shoulder, halter-neck or with straps narrower than an inch are off limits." Yikes.

If anyone were to see Princess Diana playing with Prince Harry while wearing a pair of overalls, they'd say that she looked like a mom on the go. But Diana was defiant, even in her most casual of looks, and the light blue denim overalls that she chose to wear to a polo match defied expectations of what she should have worn to such an event. 

As noted by PopSugar, the outfit was cute — Diana paired the overalls with a simple white button down and loafers, and she really did look like every other mom dressed for function and comfort. But polo matches, from what we can tell, serve as a who's who in the royal world. Not only did Diana break the no pants and the no denim rules, but she didn't conform to what people expected her to wear. 

Years later, we've been able to see how Diana's sons and their wives have dressed for polo matches. Even with three little kids, Kate Middleton wore a pink dress from luxury designer L.K. Bennett and heels — pretty different than Diana's dungarees.

Princess Diana made it clear that she was a mom before she was anything else. As such, the public were treated to some of her best casual mom outfits, and although they were deemed highly inappropriate for a royal, her choices were iconic. As noted by Livingly, Diana often paired pants with cowboy boots and a baseball cap. 

Sometimes (prepare yourselves) she even chose comfier options. As noted by Insider, Diana was spotted dropping off her sons at school in 1989, and she wore the most quintessential mismatched mom outfit: a sweatshirt, sweatpants, cowboy boots, a blazer, and a baseball cap. If you were to describe that outfit to anyone, they'd likely say that the person wearing such an ensemble was guaranteed to look a mess. But Diana pulled it off in the effortless style she had, and we couldn't love her any more for it. 

So the next time you're running out the house in a pair of old jeans, a sweater that belonged to your ex, and a pair of Vans you should've thrown away years ago, just remember that a princess basically rocked the look first.

We'll certainly hand it to her, the queen has a style all her own and has seemed to always be conscious of covering up. But that is a memo that Princess Diana did not get, and while she was part of the royal family, she consistently defied the odds. One such dress that shook up the royal dress protocols was the Catherine Walker gown she wore while on a trip to Brazil in 1991, according to Insider. 

In good old 1990s style, the dress consisted of a column silhouette and featured a one-shoulder neckline (yes, one of her shoulders was completely exposed). The gown featured a floral beaded design and hugged the princess' figure in all the right places. So needless to say, the dress has since been dubbed one of the most daring outfits ever worn by a royal. 

Exposing your shoulders is still a big deal in the royal family. Meghan Markle came under intense fire when she wore an off-the-shoulder look to the Trooping the Colour in 2018, as noted by People.

Princess Diana Spencer redefined what royals could and couldn't do with their wardrobe, and the same mentality applied to her approach to jewelry. The royal family's jewelry is not to be messed with (traditionally), but Diana rewrote the rules. 

As noted by People, she was loaned a diamond and emerald choker — featuring the coveted Cambridge emeralds — by none other than Queen Elizabeth herself. The piece was created by Queen Mary and, as such, had a rich royal history. Diana wore the piece frequently while married to Prince Charles, as the queen rarely wore it herself and lent it to Diana often. 

But here's where things get crazy. Diana was spotted wearing the choker as a headband, completely repurposing the heritage jewelry piece and how it was supposed to be worn. You might think that simply switching up how you were a piece of jewelry isn't a big deal, but to this day, royal women have to abide by strict jewelry protocols: no diamonds during the day and no tiaras until your wedding day, so it's fair to say that Diana challenging the history of such a storied piece of royal jewelry was not looked upon fondly.

If one image of Princess Diana Spencer has stood the test of time, it's the photo of her arriving at the Serpentine Gallery gala in 1994. She looked stunning in the form-fitted black chiffon dress that just barely skimmed her knees, and she paired the look with black stockings, black pumps, stunning jewelry, and, of course, her effortless poise. So what made the look so inappropriate? The context of the day, really. 

As noted by People, Prince Charles had admitted (on national television, we might add) that he had been cheating on Diana that afternoon. And instead of letting the confession get the best of her, she stepped out in one of her most daring outfits of all time. "On a human level for Diana, you can only imagine how upsetting that would have been, not only to hear that but to know that now the world has heard it," People's senior editor, Michelle Tauber, said. "Some may have decided this was altogether too much and tried to avoid the cameras, stay out of the limelight — just let the storm pass. That is not what Diana chose to do that night."

The Serpentine Gallery galas and parties really saw some of the best Princess Diana outfits, and this number she chose to wear in 1995 broke so many royal protocol rules, it's hard to know where to start. The dress itself was a gorgeous powder blue and featured a plunging halter neckline, a short hemline, and a squared-off backless silhouette. She carried a small silver clutch and topped off the dazzling look with dropdown earrings and a delicate bracelet. 

So what's all the fuss? Well, the dress was very inappropriate by royal standards — let's dive in. The skirt was far too short to conform to royal protocol. Necklines in the royal family almost always cover the shoulders and are never plunging, so there's two more rules broken right there. To top it off, Diana was not wearing pantyhose, a staple royal dress tradition that is still followed by the royal women to this day. 

All of Diana's decisions were heightened at the time, as she was going through divorce proceedings, as noted by Insider. But it's clear that she knew what she was doing.

If we could model our closets after Princess Diana, we would — her iconic collection of sweatshirts, ranging from her Harvard design to her Atlantic pullover, continue to inspire the best casual outfits out there. But Diana really challenged the rules when she wore a sweatshirt with U.S.A. and the American flag printed on the front. 

As noted by Cosmopolitan, the royals do not often show a love of country quite like Diana did, even when traveling diplomatically. It's common for a member of the royal family to pay subtle homage to other countries (like when Kate Middleton wore a maple-leaf hat on Canada Day), but to go as far as wearing a sweatshirt that most of us would choose for the Fourth of July is a whole different ball game. 

Despite the clear defiance that Diana was displaying with her casual look, people still adored her style and, as such, were eager to pay top dollar for pieces of her wardrobe. A similar U.S.A. sweatshirt in Diana's closet was expected to sell for over $10,000, as noted by People. We'll stick to Gap for our U.S.A. looks.

Biker shorts with an oversized sweatshirt is all the rage, but Princess Diana Spencer started the trend. Spotted on occasions exiting the gym, Diana wore skin-tight biker shorts, sunglasses, and messy hair, and we couldn't love her more for it. But the look was highly inappropriate for a member of the royal family, and even after her divorce from Prince Charles, it seemed as if the royals still expected Diana to dress like they did — but that, of course, was not how things went. 

Her iconic outfit of biker shorts and a navy blue sweatshirt clearly captured the attention of many, and, as noted by Vanity Fair, the sweatshirt itself sold for $53,532 at auction in 2019. "The piece was special not just because Princess Diana wore it," Vanity Fair reported, "but because she used it." 

It seems like workout attire isn't even included in royal dress protocols, probably because the royals never dreamed that someone associated with them would go out in public in such a casual outfit. As noted by Cosmopolitan, even jeans are considered off limits and are only acceptable for dog walking and other super casual events. We'll choose the commoner's life and bike shorts any day.

In her early days as a royal, Diana Spencer was very timid, and she even earned the nickname "Shy Di" as a result. But one of the ways she broke out into the spotlight was with her clothing, and this look in 1983 really defied the expectations of the young royal (and arguably set the stage for all the groundbreaking looks she would choose after that). 

While attending a ballet gala in New Zealand, Princess Diana opted for a silk taffeta gown by designer Donald Campbell that featured an off-the-shoulder neckline (via Tatler). The gown was a gorgeous purple color and looked as delicate as Diana did — but it still broke the "don't show your shoulders" rules. 

As her sons have gotten married and their wives have carved fashionable spaces of their own, it seems like some royals who break the rules are more criticized than others. As noted by Insider, Kate Middleton has often been seen in off-the-shoulder dresses, but the choices largely go unnoticed unlike those made by Meghan Markle, who has come under intense fire for breaking the protocols. But like Diana, Markle seems to be a force to be reckoned with.

If we learned anything from Diana Spencer, it was that royal dress rules were meant to be broken. She often opted for dresses that were above the appropriate hemline, that featured necklines deemed scandalous, and that did not feature pantyhose (the horror). 

And as she defied the expectations with every outfit, Princess Diana picked up a couple of tricks that helped her avoid wardrobe malfunctions or unflattering angles — specifically, she used her clutches as "cleavage bags," and often used the accessory to hide her chest as she was exiting vehicles. As noted by Cosmopolitan, her handbag designer Anya Hindmarch coined the term "cleavage bags," and spoke to The Telegraph about the trick. 

"We used to laugh when we designed what she called her 'cleavage bags,' little satin clutches which she would cover her cleavage with when she stepped out of cars," Hindmarch said. "And in photos, every time Princess Diana got out of a car, her clutch was right there to shield her chest from prying photographers. So clever!"