How Princess Diana's Wardrobe Changed After Leaving The Royal Family

After Princess Diana joined the royal family in her 1981 marriage to King Charles III, the world took note of her style. As time went on, her fashion sense developed and bloomed. While the late princess was always iconic, the way she dressed majorly shifted once she left the royal family in 1996. As she found more freedom, she began to truly express herself through her clothes and break away from some of the restrictions that came with being in the royal family.

From strict rules about what nail polish colors to wear, to how to dress in casual settings, there were a lot of royal dress codes to follow. That said, things like going without pantyhose or wearing an above-the-knee skirt were all rules that Diana left behind when she left the royal family. It wasn't just the little details that changed, though. Diana's style became simpler, more sleek, and modern. Many of the prints, patterns, and ruffles she wore in the past went by the wayside as she opted for more minimalist and fitted clothing. Not only that, but she found ways to elevate casual outfits into something timeless and memorable. Even though Diana may not have had a long period of time free from the royal rules, she still showed the world how to dress with a boldness and elegance that is still captivating decades later.

While Princess Diana and King Charles III may have announced their separation in 1992, it wasn't until August of 1996 when their divorce was finalized, and Diana was officially no longer part of the royal family. This meant more freedom in lots of different ways, but particularly when it came to how she dressed. Even though she'd been playing around with more daring looks before actually leaving the royal family (the iconic revenge dress she wore in 1994 being a prime example), now she was completely free to dress herself on her terms.

While attending a ballet event in 1996, she could be seen wearing a light-blue skirt suit with white piping. This look in particular is a great example of a style staple for Diana in the coming months. Skirt suits were a frequent choice for her, and after she left the royal family she began opting for simpler styles, and shorter skirts more than ever before.

Another notable facet of Princess Diana's post-royal style choices was that she was starting to show more skin. At a 1996 humanitarian event in New York, Diana wore a low-cut black gown with subtle beading on the chest. Not only did she pull off the more daring look with ease, she looked totally confident, too. Later in 1997, she was pictured in New York in a white floral print minidress with beading that also featured a much lower neckline than she would have ever worn while still part of the royal family.

While some might focus on the revenge dress that Diana wore to the Serpentine Summer Party on the same night that King Charles III admitted to adultery on national television, the reality is that from the time she left the royal family until her untimely death, she was dressing for revenge on a regular basis. Not only are her more daring necklines an indicator of this, but there's also evidence in the way that she truly glowed and looked at ease in her own skin.

It wasn't just the cuts or lengths of Princess Diana's dresses and suits that were changing; she was making some subtle shifts in her fashion choices, as well. While lace may have always been a part of her wardrobe, she was now ditching over-the-top frills for more sultry styles of lace. The most noteworthy example of this is the slinky, elegant dress that she wore to the 1996 Met Gala.

Just a few weeks before her divorce was finalized, Diana donned a long, night-gown-inspired look designed by Dior and paired it with a massive multilayered pearl choker and some earrings with blue gems. Even though a long navy gown might not have seemed all that wild, wearing something with lingerie-like details was definitely not something the royals would have likely approved of.

Another detail that highlighted Diana's newfound freedom was her choice of accessories, and in particular, handbags. While part of the royal family, Diana was required to only wear clothes and accessories from local designers. Once on her own, she started carrying a small black Dior bag, which eventually became the "Lady Dior" bag in her honor. Fashion journalist Sarah Mower wrote for the Daily Mail that Diana's decision to carry bags from European designers such as Dior, rather than the royal-favored English brand Launer, "was a symbol of independence" following her departure from the royal family. 

Blazers were always a style staple for Princess Diana, however, in the months after her divorce, she took this look in a new direction. Not only did she wear blazers in bold shades of red, but she started wearing them in simpler cuts with a more no-nonsense feel to them. After leaving the royal family, Diana wasn't just attending parties or reveling in the single life — she was also taking on philanthropic work. She was involved with a range of charities, including the homeless charities, hospitals for sick children, and the National Aids Trust.

Naturally, this meant that she needed to dress in a way that conveyed the importance of the work she was doing. While some of her skirt suits from this time may have been fitted and flattering, they also looked incredibly professional and put-together. The red blazer and skirt that she wore while visiting a hospital is a great example of how Diana managed to look stylish while taking into consideration the seriousness of the work she did. According to Elizabeth Holmes, author of "HRH: So Many Thoughts on Royal Style," Diana loved to communicate through her wardrobe. Talking to Business Insider, she said, "I think Diana's choices were screaming sometimes. Diana delighted in clothes. Her story is filled with such highs and lows, but understanding her fashion, how she used it, found power in it, and reclaimed her voice is my favorite part of this book."

Low-cut necklines weren't the only way that Princess Diana showed off more skin. Sleeveless dresses, especially minidresses, were another big feature in her new wardrobe. While visiting Sydney, Australia, Diana wore a short purple shift dress, which she paired with multiple strands of pearls, a nude bag, and some nude heels. The outfit highlights her ability to pair her more playful style with classic details to create a well-rounded look.

Although she may have gone sleeveless more often after leaving the royal family, sleeveless dresses had already begun to make more frequent appearances in her wardrobe as early as 1995, when she and King Charles III were separated, but still not legally divorced. A lacy, light-blue halter dress designed by Catherine Walker that she wore to a 1995 Vanity Fair dinner is a great example of this, as is a summery, fun white Versace minidress she wore to a charity concert in Italy.

Despite keeping herself busy, Princess Diana had time to relax and rock some truly daring swimsuits. After leaving the royal family, paparazzi snapped plenty of pictures of Diana hanging out on the beach in some truly eye-catching swimsuits. Sometimes consisting of low-backed one-pieces, other times bright-colored or wild-printed bikinis, Diana's swimsuit style was every bit as interesting as the gowns or suits she wore to major events.

In fact, her swimsuits are so iconic that they're still making cultural waves today. Her animal-print one piece, in particular, is getting plenty of attention, due in part to Season Six of the Netflix series, "The Crown" where Diana wears the distracting swimsuit to keep paparazzi focus away from her children. The swimsuit got so much attention that the brand Gottex has made another version of the animal-print one piece. 

Speaking of the significance of one of the most iconic Princess Diana outfits that "The Crown" recreated perfectly, costume designer Sidonie Roberts said to People, "If you look at the wedding dress, which is humongous and very over the top, and then you get to the revenge dress and then you strip it right back to the swimwear there's this sense of exposing and allowing yourself to unfold. There's an actual unfolding. We said it [was] like the cocooned butterfly."

Along with skirt suits, pantsuits were a regular fixture in Princess Diana's multifaceted wardrobe. While attending the auction of her gowns in New York in 1997, Diana wore a refined and low-key camel-colored pantsuit. She'd also been snapped wearing light-gray power pantsuits with small ruffle details to casual lunches and dark-gray pinstriped variations while leaving airports. While visiting Pakistan, Diana donned a traditional Pakistani outfit called a shalwar-kameez which bared a lot of similarities to her typical power pantsuits. Of course, Diana didn't just start wearing pantsuits right after she left the royal family. In fact, she was the first royal woman to wear a pantsuit to an evening function, which was a truly trail-blazing move at the time.

While speaking to Woman & Home, Simra Khan-Jackson, owner of Vulture London, had a lot to say about the significance and impact of Diana's pantsuits: "Diana's power-suits mirrored her bold, unique, and influential personality. They not only looked ultra-stylish but were also practical, allowing her to carry out her duties as a princess, which were not always glamorous." Khan-Jackson added that Diana had a "nonconformist attitude" and that "her power-suits were designed to fit her unapologetic and confident personality."

Breaking ties with the royal family meant Princess Diana had the freedom to dress how she wanted, but not just when it came to styles or cuts. She had the freedom to wear the designers she wanted to as well. While still part of the royal family, Diana was required to wear local designers, the exception being that she could wear foreign designers while visiting their country, as a diplomatic gesture. However, by 1996, Diana was donning clothes from a wide range of fashion houses.

During an interview on "Lorraine," Eloise Moran, the author of "The Lady Di Look Book: What Diana Was Trying to Tell Us Through Her Clothes," explained Diana's blossoming, international style, and broke down the significance of the iconic purple Versace dress Diana wore in 1996. She said, "She definitely developed a more jet-set, international look, and Versace was one of the key players in these amazing looks. It was very streamlined, you can see she wasn't afraid of showing off her body more," per Express.

Along with that, Moran gave an interesting tidbit about why Diana was also wearing higher heels now, too, saying "She was wearing high heels as she used to stick to quite low heels with Charles because they were the same height."

The shiny blue Versace gown that Princess Diana wore while visiting Australia is another great example of the new risks she was taking. More and more, Diana was shifting away from prints, frills, and patterns post-divorce. She was also moving away from bulkier or looser clothing, and selecting fitted gowns that accentuated her figure. Comparing the outfits that she wore on her first trip to Australia as a royal with the ones she wore on her trip there in 1996 is a great way to see the overall changes in her wardrobe more clearly.

Unlike her first trip where she wore layered prints and elaborate evening wear, during this trip she frequently wore simple skirt suits. Even her evening gowns had a more understated feel, despite their bold and eye-catching colors. Diana often went for monochromatic looks, matching her high heels and her clutches exactly to her dresses. In comparison with the busy looks of her past, these new styles reveal a version of Diana that was unafraid to be herself.

Not all of Princess Diana's fashion was about looking ultra-glamorous. Some looks she wore in her newly found freedom were more comfort-focused. Still influencing athleisure today, Diana's bike shorts and crew neck combo is the epitome of looking classy while being comfortable. Not only was this a simple but solid style, but Diana also incorporated it into her fashion rotation pretty frequently. By pairing a large graphic sweatshirt with bike shorts, sneakers, and slouchy Princess Diana socks, she created a laid-back gym look with a lot of room for trying out different variations. From neon orange and pink bike shorts paired with collegiate sweaters to simple black shorts paired with pale-blue graphic sweatshirts, Diana often got playful with her color pairings.

That said, there was one bike-shorts outfit that she wore on repeat, for a very specific reason. While appearing on Yahoo!'s "The Royal Box," Diana's trainer Jenni Rivett mentioned that one of the clever ways that Diana used her wardrobe to mess with the paparazzi and make their photos of her less valuable: "I remember one of her strategies was that she was going to wear the same Virgin sweatshirt every single session."

In her time away from the royal family, Princess Diana's looks didn't just become more bold; many of them took on a new and more modern type of elegance. While Diana had always known how to have fun with her clothes, she was now opting for looks with feminine details that were somewhat more subtle, though no less charming. To a 1997 performance of "Swan Lake" at the Royal Albert Hall, Diana wore a pale-blue minidress covered in delicate beading. Sticking to her monochromatic styling, her heels and clutch were also light blue, and her pearl necklace was glamorous while still being low-key, proving that she was a master at finding modern ways to pull pearls into her wardrobe.

The same year, Diana wore another refined but eye-catching outfit: a spring-green Chanel skirt suit which she paired with beige heels and a beige purse. The fact that Diana was wearing Chanel was yet another sign that she was moving forward from her marriage and her past as a royal. It had been reported that Diana avoided wearing Chanel for a period, because the linked C's reminded her of the initials of King Charles III and Queen Camilla, the woman he had an affair with. It seems, though, that Diana had put that behind her and had no problem rocking bright and feminine Chanel suits.

In the time after her divorce, Princess Diana put as much care into her off-duty outfits as she did the gowns she wore to events and balls. This is illustrated by one of her signature casual looks. While in Bosnia raising awareness for landmines, she paired a white button-up blouse with a pair of light jeans and tan loafers (which are some of the absolute best shoes to pair with your favorite mom jeans). Even though the outfit was incredibly low-key, it had the unmistakable sophistication that makes quiet luxury so appealing. It became a truly iconic look, however, it wasn't the only time that she wore jeans.

Paparazzi often snapped Diana in denim, sometimes wearing a basic white tee and a dark coat, or paired with a neutral blazer and shoes. Diana always had great instincts when it came to styling denim, but in the time after her divorce, she took it to a new level. Not only did she manage to wear jeans that were just as sophisticated as they were casual, but she created looks with a timelessness that is still inspiring and influential today.