Princess Diana's Most Risqué Outfits, Ranked

When she started dating King Charles III, Diana Spencer didn't aspire to be an influential style icon who would break the British monarchy's sartorial chains, but that's exactly what happened when she became the ninth Princess of Wales. While nothing she stepped out in was quite as revealing as the inappropriate outfits worn by celebs such as Britney Spears, several of Princess Diana's outfits were considered racy — for a royal.

Upon joining The Crown, Diana often channeled a quintessential fairytale princess in decadent confections — skirts were full; sleeves were puffy; and gowns were overstuffed with ruffles and frills. Because Diana was a fashion novice, former British Vogue deputy editor Anna Harvey was tasked with helping her put together a wardrobe fit for a future queen. In a 1997 essay for her magazine, Harvey recalled that her young charge did not prioritize style, but Diana eventually became a savvy dresser. "She quickly learned how to use her image to communicate her messages and goals," said Eleri Lynn, the curator of Kensington Palace's "Diana: Her Fashion Story" exhibition, in a BBC interview.

As she found her fashion footing, the princess would become a trendsetter; in fact, Kate Middleton has channeled Diana with her wardrobe choices before. Diana also set a precedent for the other daughter-in-law she never got to meet, Meghan Markle, by changing her style after leaving the royal family. And when Diana decided that royal fashion rules are meant to be broken, she hiked up her hemlines and deepened her necklines to create some of her 10 most risqué ensembles.

Princess Diana had one of her first close encounters with the British media in 1980. She was working as a preschool teacher at the time and had a wardrobe befitting her profession. "She wore longer skirts and sort of frumpy sweaters," Elizabeth Holmes, the author of "HRH: So Many Thoughts on Royal Style," told WWD. Diana was wearing such an ensemble when The Sun photographer Arthur Edwards tracked her down at the Young England Kindergarten School in Pimlico and photographed her. As the clouds in the sky parted, he scored some images that have since become iconic.

In an interview with "Today," Edwards insisted that he was not aware of how sheer Diana's patterned skirt was when he began snapping away. "Everybody doesn't believe this, but it is the gospel truth — halfway through, the sun came out and revealed those beautiful legs," he recalled. However, he had to have known that Diana, who was 19 at the time, would be mortified when she saw how the sunshine and the skirt had conspired to commit such a serious betrayal of her modesty. He defended himself by saying, "I didn't do it to embarrass her, but it was such a good picture you couldn't not publish it."

Other photographers had descended upon the school and taken similar photos. In a piece for the Daily Mail, Charles Rae, a former royal correspondent for The Sun, explained that his publication and a rival had negotiated a rather unethical deal with Diana and her employer: she had to make herself available for the pictures if she didn't want reporters to hound her at work. Upon seeing the photos, Diana reportedly lamented to her future husband, "I don't want to be known as the girlfriend with no petticoat."

Princess Diana was once known as "Shy Di," but one of her early wardrobe choices earned her a new moniker: "Daring Di." In 1981, she accompanied King Charles III to her first public engagement as his fiancee, a concert at Goldsmiths' Hall. All eyes were on her, so imagine everyone's shock when she showed up in a dark frock that looked more like something that would be found in the closet of a deliciously devious Disney villainess rather than a princess-to-be.

The taffeta ballgown was created by David and Elizabeth Emanuel, the design team behind Diana's celebrated wedding dress. In the documentary "Diana: Queen of Style" (via Express), Elizabeth revealed that the gown was not designed with the future royal in mind; Diana had seen it at the Emanuels' shop and instantly been enchanted by it. It was strapless with a low, ruffled neckline that was rather scandalous at the time. "It was a controversial outfit. It focused the eyes of all the fashion journalists," Elizabeth recalled. She also told the Daily Mail, ”We hadn't considered the fact that when Diana bent over — as she would have to do when getting out of the car — she would show quite a lot of cleavage."

In his biography "Diana: Her True Story — In Her Own Words," Andrew Morton shares some of Diana's commentary about the gown. "I was quite big-chested then and they all got frightfully excited," she remembered. She also said that Charles disliked the garment because it broke the royal dress code: it was black, a hue his family reserves for mourning. Diana's argument was that she wasn't yet a royal, but in the years to come, the defiant princess would continue to wear the color.

At the 1996 Met Gala, a recently divorced Princess Diana showed up in a slinky slip dress in midnight blue. It would be considered tame by today's standards, but the black lace trim on the neckline, skirt, and slender shoulder straps scandalized some fashion critics at the time. "The problem, and there is no delicate way of saying this, is that it looked like she had accidentally stepped out in her nightie, which meant, of course, that she wasn't wearing a bra," read a review by the Daily Mail's Brenda Polan.

According to the Daily Mail, Diana almost backed out of wearing the body-skimming garment because she feared that a young Prince William would not approve of the look — he was a teen at the time, so he was more inclined to be embarrassed by his parents' behavior. However, Diana didn't just wear the Dior dress; she altered it in a way that made it more revealing.

In the documentary "In Vogue: The '90s" (via InStyle) John Galliano recalled working with Diana to create the gown as Dior's freshly minted creative director. He revealed that Diana was resistant to his plea for her to wear pink, and he was stunned when he saw that she had removed the dress' built-in corset. There's no word on William's feelings about this change, but it got Galliano's approval. "The dress was much more sensuous," he said. "The cameras went mental."

Fans of Princess Diana came to expect her to serve lewks that were elegant, sophisticated, and romantic, which may explain why one of her most enduring contributions to the fashion lexicon is a now-classic casual combo: bike shorts and an oversized sweatshirt. Vogue Australia noted that Diana's tiny, tight bottoms were the first time the strict royal protocol for wardrobe had been violated with athleticwear. The magazine also pointed out that modern royals are rarely spotted out and about in their workout clothing (nor are they often seen exposing so much leg). But if they were to hit the gym in Diana's aforementioned outfit, they'd always look on-trend.

Outside the Chelsea Harbour Club where she exercised, Diana was regularly photographed wearing the same dark blue "Fly Virgin Atlantic" sweatshirt with her stretchy shorts. In an appearance on the Yahoo! series "The Royal Box," Diana's trainer, Jenni Rivett, explained that her client stepped out in the athletic ensemble over and over again to frustrate the paparazzi; it made their photos stale and repetitive, decreasing the images' value. "I thought that was very clever of her," said Rivett.

Diana received her famous cozy top for free from Virgin Atlantic airline founder Sir Richard Branson and later re-gifted it to Rivett. In 2019, the trainer sold the garment for over $50,000 at an auction and donated the money to a family in need, an act of kindness of which her late philanthropic friend surely would have approved.

A few years into her marriage, Princess Diana entered her "Dynasty Di" era by deflating her silhouettes. She eschewed voluminous fairytale dresses and started wearing sleek, streamlined styles that were more glamorous and sexy, such as the silver lamé dress she sported to several events in 1985, including the premieres of the movies "Burke & Wills" and "A View to a Kill." It was also her gown of choice for a benefit hosted by its designer, Bruce Oldfield. At the event, she actually rubbed shoulder pads with one of the women who helped popularize her new fashion aesthetic, "Dynasty" star Joan Collins.

Diana also hit the dance floor in her pleated garment, which featured a deep but slim V-neck. One way she turned her back on royal tradition was with the addition of a large, triangular cutout on the back. According to a news report from the time shared on the Princess Diana News Blog, the royal dished that this detail made dancing a delicate undertaking. "People, when they guide you, sometimes don't know where to put their hands!" she said. Her dance partners that evening reportedly included "Superman" actor Christopher Reeve.

While Diana dazzled in her metallic dress, Oldfield insisted that she never wanted to be a glamazon. "I think for all of us there was always this problem that there wasn't a clear idea of how she should dress," the designer told British Vogue. "She was aware that even in some far-flung part of the world she was representing Britain, and she couldn't be a glamorous clotheshorse." That was one endeavor at which she clearly failed.

Long before Kate Middleton got the internet buzzing by showing off her killer legs, Princess Diana started shortening her skirts. As she continued basking in her freedom from the constraints of royal life, the divalicious divorcee decided to do a little closet clearing in 1997 — she had to make room for some of her newer, more alluring apparel, after all.

Proving that she was more than ready to put royal life in the rearview mirror, Diana placed dozens of her gowns up for auction at Christie's, with the proceeds from their sale going to charity. While the garments were iconic pieces of history, they were also reminders of The Firm's strict fashion rules and Diana's failed marriage. She made another statement by bidding her old gowns adieu in a pale blue sheath dress by a designer she frequently worked with, Catherine Walker. Its skirt hit a few inches above the knee, and it featured tank-style sleeves and a low scoop neck. "Wearing a short dress was definitely a bold move for the Princess of Wales, who was restricted from doing so when she was still married to then-Prince Charles," Daena Borrowman, a marketing manager for jewellerybox, told Express.

Among those who attended the auction was late comedian Joan Rivers, who was probably a bigger fan of the skimpier garment than any of the more substantial looks available for bidding. ”It's interesting to see how her style, thank God, changed,” the "Fashion Police" star told The New York Times.

Royals are not immune from wardrobe malfunctions, and Princess Diana realized that exposing more of her décolletage was a risky endeavor — every time she exited a vehicle, photographers' lenses would be trained a bit below her collarbones. This is when she required assistance from one of her favorite accessories. "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," handbag designer Anya Hindmarch recalled to The Telegraph (via Glamour).

Diana used this style hack in 1997 when she showed up at the Royal Albert Hall to watch a performance of the ballet "Swan Lake." For the event, she wore a low-cut Jacques Azagury minidress in powder blue. It was dusted with shimmering beading. Azagury told The Telegraph that it was one of Diana's favorite looks that he created for her. "She actually wanted to go shorter because she loved what the supermodels were wearing at the time, but we stopped her at four inches above the knee," he recalled.

The designer told People that Diana was meticulous about her outfits when he worked with her. She knew that her adoring public cared about her clothing, and she wanted every detail to be impactful. With Azagury's blue dress, she wore a pair of matching Jimmy Choo heels that Carrie Bradshaw would have built a shrine to if she had managed to get her hands on them. However, the brand was still in its infancy when Diana slipped on a pair of its now-signature sling-backs. "It really started everything for us — all of the celebrity appearances," creative director Sandra Choi told Marie Claire.

In 1988, Princess Diana was photographed looking like she was participating in a fashion shoot while aboard a yacht in Majorca, Spain. She had on a bandeau bikini that featured a bold floral print, and she couldn't have asked for better lighting — the way the sunshine glinted off her tousled gold tresses and tan limbs looked like the work of a master photographer who had tirelessly pursued the perfect shot.

A year prior, the paparazzi had snapped pictures of Diana in the same locale wearing a similar two-piece, and she got brutally body-shamed. "Di's bikini pot-belly on a Majorcan beach this week drew gasps of amazement as she let it all hang out," the now-defunct tabloid News of the World captioned a photo of Diana playing in the water with her two sons. Journalist Clive Goodman, who was later arrested on phone hacking charges, also penned a column opining that she looked pregnant. However, he suggested that she had possibly gained weight due to being on birth control (via the @absolutelyprincessdiana Instagram account).

In 1996, Diana was vacationing in Spain again when she was photographed sunbathing without a top. In his memoir "The Glossy Years," former Condé Nast International president Nicholas Coleridge recounts how Diana told him that Prince William was being teased at school over the ill-gotten photo, which had been published by The Daily Mirror. William's classmates had reportedly let him know what they thought about the size of his mother's chest. According to Coleridge, Diana said to him, "I want to know your real view. Are my breasts too small, do you think?" He recalls assuring her, "They seem, um ... perfect to me."

One of Princess Diana's most provocative and memorable looks wasn't one of her most revealing, but sometimes, timing is everything. On the evening of June 29, 1994, British citizens turned on their televisions and watched King Charles III confess to being unfaithful to Diana. The airing of "Charles: The Private Man, the Public Role" just happened to coincide with a Vanity Fair soiree at the Serpentine Gallery, which Diana had been invited to attend. Because of this, the clingy, off-the-shoulder LBD she showed up in came to be known as the "revenge dress."

The sexy look was seen as Diana's way of sending a message that she was not going to fade into the background anytime soon. However, it wasn't something she purchased to make such a statement. According to the garment's designer, Christina Stambolian, Diana had owned it for three years but hadn't worn it because she considered it so "daring," per Reader's Digest.

As the story goes, Diana originally picked out a Valentino number for the Vanity Fair party. But according to People, she ditched her wardrobe plans after the media caught wind of what she was wearing. In the book "Diana: A Life in Dresses," Stambolian references "Swan Lake" when reflecting on how perfect the gown she designed was for that moment in Diana's life. "She chose not to play the scene like Odette, innocent in white," the designer says (via Elle). "She was clearly angry. She played it like Odile in black. ... She was saying: 'Let's be wicked tonight.'"

Princess Diana returned to the scene of her sartorial slayage a year later. For another event at the Serpentine Gallery, she wore an even skimpier light blue dress designed by Catherine Walker. It featured a tulip hem and swirling beaded embroidery, which gave it a textured appearance.

What made the garment stand out from some of Diana's other sheath dresses, which were similarly sturdy but form-fitting, was its daring neckline. "It is almost like she is trying to outdo the dress from the year before," said "The Lady Di Look Book" author Eloise Moran in an interview with The Washington Post. "I think this was probably the first time we ever see her in a plunging neckline." Elizabeth Debicki wears a recreation of the dress in "The Crown," but it's featured in the scene where Diana attends the "Swan Lake" performance.

Walker designed hundreds of looks for Diana, so she became intimately acquainted with the princess and what she wanted to convey with her style. "She was desperate to get a more serious image and Catherine Walker was indispensable in helping her forge one," Anna Harvey recalled for Vogue. But Diana also dressed to impress, and she gave her admirers an astonishing amount of phenomenal fashion moments to serve as timeless style inspo before her tragic death at age 36 in 1997. Royal fashion expert Elizabeth Holmes told WWD, "She did something within her very short, and jam-packed time that few could do. And her clothing was a big part of that."