Sophia Michaels
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When Diana Spencer started her romance with King Charles III, she had no intention of becoming a fashion trendsetter who would challenge the norms of British royal attire. Yet, upon becoming the ninth Princess of Wales, she did just that. While her looks may not have reached the extremes of pop culture icons like Britney Spears, several of Diana’s outfits were undeniably bold for a royal.
Initially, Diana adopted a classic fairytale princess aesthetic, often seen in elaborate dresses with voluminous skirts and elaborate sleeves. As someone relatively new to fashion, she received guidance from Anna Harvey, then-deputy editor at British Vogue, to curate a queenly wardrobe. Harvey noted in a 1997 essay that while Diana wasn’t initially focused on fashion, she eventually learned to leverage her image effectively. Eleri Lynn, curator of Kensington Palace’s “Diana: Her Fashion Story” exhibition, explained in a BBC interview that Diana quickly transformed into a savvy fashionista.
Over time, Diana became a fashion icon; her style has inspired figures like Kate Middleton and even influenced Meghan Markle, who adapted her fashion after stepping back from royal duties. When she began to defy royal fashion conventions, Diana elevated hemlines and neckline depths, leading to some of her most daring outfits.
The Drama Behind a Modest Outfit
In 1980, during her time as a preschool teacher, Princess Diana had a notable run-in with the media. At this point, she was dressed in a manner typical for her job, sporting longer skirts and simple sweaters. According to Elizabeth Holmes, author of “HRH: So Many Thoughts on Royal Style,” it was during a visit to Young England Kindergarten School that she was photographed by The Sun’s Arthur Edwards. This encounter would lead to some iconic images.
In a later interview with “Today,” Edwards claimed he was unaware of the sheerness of Diana’s skirt while shooting. “People don’t believe it, but it’s true—when the sun broke through, it revealed her beautiful legs,” he recounted. However, he recognized that Diana, then just 19, might feel embarrassed by the exposure. He justified his actions by insisting the photograph was too good not to publish.
Other photographers were present and captured similar moments. Charles Rae, a former royal correspondent for The Sun, discussed in the Daily Mail that an unethical agreement was made between Diana and her school: she had to pose for photos to avoid harassment from reporters. Following the publication of these images, Diana reportedly confided to Charles, “I don’t want to be seen as the girlfriend without a petticoat.”
Diana’s Daring Ballgown Made Headlines
Once referred to as “Shy Di,” one dress moment led to a shift in how the public viewed her: she became “Daring Di.” In 1981, attending her first public engagement with King Charles III at a concert, her outfit turned heads. She arrived in a striking dark gown that seemed more suited to a villain than a future queen.
This stunning taffeta gown was designed by David and Elizabeth Emanuel, the same team behind Diana’s iconic wedding dress. In the documentary “Diana: Queen of Style,” Elizabeth shared that the gown wasn’t initially intended for her; Diana fell in love with it the moment she spotted it in their shop. Strapless with a low neckline, it was considered quite daring for its time.
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According to Elizabeth, the outfit caught the gaze of many fashion journalists. She shared with the Daily Mail that they hadn’t anticipated how much cleavage would be exposed when Diana leaned to exit a vehicle.
In his book “Diana: Her True Story — In Her Own Words,” Andrew Morton recounts Diana’s reflections on the dress. She noted, “I was rather well-endowed then, and everyone got extremely excited.” Furthermore, she mentioned that Charles was not a fan of the dress since it violated royal fashion rules by being black, a color typically reserved for mourning by his family. Diana countered that she was not yet part of the royal family, and in future years, this bold choice would become a signature color for her.
Concerns Over Met Gala Dress’s Impact on Prince William
At the 1996 Met Gala, a newly single Princess Diana appeared in a striking midnight blue slip dress. While seen as less provocative today, the dress’s black lace embellishments on the neckline and straps raised eyebrows among fashion critics at the time. Brenda Polan from the Daily Mail remarked that it appeared Diana had made a fashion faux pas, akin to wearing her night wear without a bra.
Diana reportedly contemplated withdrawing from wearing the revealing design, concerned about her teenage son Prince William’s potential embarrassment over her bold choice. Ultimately, she not only wore it but also made it even more revealing.
In the documentary “In Vogue: The ’90s,” designer John Galliano revealed how Diana, who was averse to his suggestion of pink, surprisingly removed the dress’s built-in corset. Although it’s unclear how William responded to the alteration, Galliano approved, praising the dress’s more sensual look that captivated the media. “The cameras went wild,” he noted.
Pioneering Athleisure Style
Princess Diana was known for her elegant and sophisticated fashion choices, but she also made a significant impact in the realm of casual attire by popularizing a classic look: bike shorts paired with an oversized sweatshirt. As noted by Vogue Australia, her athletic wear represented a stark shift from the royal dress code. In contrast, modern royals are seldom seen in workout gear or sporting such leg-exposing outfits.
Diana often wore a navy “Fly Virgin Atlantic” sweatshirt while exercising at the Chelsea Harbour Club. Her trainer, Jenni Rivett, shared in an appearance on Yahoo! series “The Royal Box,” that Diana repeatedly donned this outfit to outsmart the paparazzi, making their images less valuable. Rivett praised Diana’s clever strategy.
The iconic sweatshirt, a gift from Virgin Atlantic founder Sir Richard Branson, was eventually donated by Rivett to auction, fetching over $50,000. The proceeds were given to a family in need—a charitable act Diana would likely have supported.
A Dress That Made Dance Partners Uneasy
As her marriage progressed, Princess Diana embraced a new fashion approach dubbed her “Dynasty Di” phase, which featured more structured and alluring outfits. This transformation began with sleek designs, moving away from the traditional voluminous styles typically associated with royal appearances. One notable piece was a silver lamé dress, which she wore to various high-profile events in 1985, including the premieres of “Burke & Wills” and another film…
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“A Dazzling Evening: Princess Diana’s Bold Fashion Choices”
During a benefit hosted by designer Bruce Oldfield, Princess Diana made a memorable impression in her stunning metallic gown, reminiscent of fashion seen in films like “View to a Kill.” At this event, she mingled with notable personalities, including “Dynasty” star, Joan Collins, who played a significant role in influencing the fashion trends of that era.
The gown was designed with a sleek V-neck and a striking triangular cutout at the back, diverging from traditional royal attire. This daring design detail had its challenges, as Diana humorously noted, “Sometimes people don’t know where to put their hands!” Her dance floor highlights reportedly included shared moments with actor Christopher Reeve.
Although Diana exuded glamour in her dress, Oldfield emphasized that she did not aim to be overly glamorous. He reflected on the difficulty of defining her style, noting her awareness of her representative role for Britain, which shaped her fashion choices throughout her public life.
She Bid Farewell to Tradition with an Auction
In a bold move well ahead of the royal trend, Princess Diana began to shorten her skirts, particularly in 1997 when she cleared out her closet to make way for more contemporary looks. This reflected her newfound independence after her divorce.
She placed numerous gowns up for auction at Christie’s, with the sales proceeds benefiting charitable causes. This act not only signified a personal transformation but also symbolically severed ties with the royal fashion constraints that characterized her previous life. Notably, her pale blue sheath dress by Catherine Walker—a piece that was above the knee with stylish tank sleeves—was a defining representation of her evolving fashion narrative.
Esteemed guests, including comedian Joan Rivers, attended the auction, celebrating the shift in Diana’s wardrobe. Rivers expressed her happiness over Diana’s style evolution, remarking, “It’s interesting to see how her style, thank God, changed.”
Elegant Solutions for Wardrobe Malfunctions
Even royals like Princess Diana faced wardrobe challenges, particularly with revealing styles. Conscious of her public visibility, she sought inventive solutions to avoid any accidental exposure. One memorable strategy included her ‘cleavage bags’—a clever accessory to discreetly cover her décolletage when exiting vehicles, as recalled by designer Anya Hindmarch.
During a 1997 appearance at the Royal Albert Hall for the ballet “Swan Lake,” Diana wore a stunning low-cut minidress by Jacques Azagury, adorned with sparkling beads. This outfit was one of her favorites, reflecting her fondness for the bold styles embraced by contemporary supermodels. Azagury recounted how Diana had even wished for a shorter hemline, illustrating her passion for fashion.
Diana’s attention to detail was evident in her choice of footwear as well, favoring a pair of innovative Jimmy Choo heels that would go on to define the luxury shoe brand. The designer hailed this collaboration as the pivotal moment that propelled the brand into the spotlight, showcasing the lasting influence of Diana’s sartorial choices.
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