Art & Fashion

Royal Style: 39+ Photos That Prove Princess Diana Was the Queen of Fashion

As well as being history’s royal sweetheart Princess Diana is still remembered as being the undisputed queen of style. She is known and adored for being a rebel and a relentless activist. Diana, the late mother of Prince Harry and Prince William, and the late first wife of Prince Charles left a legacy of enduring popularity. But not to be overlooked is her staggering sense of fashion.

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Image: Vogue

From being scrutinized by the media for marital issues to traveling all over the globe to raising two young boys, her life had no shortage of turbulence. But through her hard work, unparalleled charisma, and friendliness, she brought love to the world. And she looked amazing the whole time she did it! Cameroon, Britain, Egypt, Canada, Norway – it doesn’t matter where and when – Princess Diana consistently wore the perfect outfit for the occasion.

Royal Tweed Is All We Need

Diana and Prince Charles are seen here smiling away in 1982 nicely bundled up for a chilly day. Diana, as always, is looking flawless. The creamy color of her Arabella Pollen coat is perfectly complemented by her Smith Jones beret. The result is that she looks super elegant.

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Image: Vogue

The coat was made for Diana when she was 20 years old. Pollen said that since he had grown up in the U.S., she wasn’t sure which direction to go with for British royalty. In the end, the gentle, light-brown tweed windowpane was perfect. Years later, Pollen noted that Diana had become empowered through fashion, and it helped her in no small part deal with the difficulties of the royal life.

Beautifully Asymmetric at the Fashion Show

Princess Diana wowed the world when she arrived at the fundraiser fashion show for Birthright at the Guildhall, London, in 1982. We’re pretty sure she must have stolen some of the models’ thunder with her beautiful midnight blue Bruce Oldfield one-shoulder dress. The pearls, the blue colors, and the pattern all remind us of the ocean.

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Image: Globe Photos

This unique and spectacular gown was not the first or the last Diana would wear that was made by Bruce Oldfield. No doubt, many of the events Diana attended were high profile. But she had a special place in her heart for Bruce Oldfield outfits. In fact, the velvet Oldfield dress she wore to dinner with the Portuguese leadership recently sold for almost 50,000 British Pounds!

American Vibes in the Park

Obviously, Princess Diana is British, but those jeans, cowboy boots, blazer, and cap have got her looking like an all-American girl. When she attended a polo match in Berkshire in 1988 with little Prince William, her outfit was a far cry from her diplomatic attire. Her sport-watching outfit is casual, yet exquisitely sharp.

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Image: The Scottish Sun

Under the sleek black blazer, Diana is wearing a British Lung Foundation sweatshirt. The red balloon on the sweater does a perfect job of punctuating the otherwise relatively achromatic sharpness of the rest of the outfit. It was a chilly spring morning, so Diana and William were bundled nicely.

Vacation In Vogue

Not all of Diana’s travels, of course, were for business, some were for pleasure. Here, she’s seen while on vacation on Necker Island in the Bahamas in 1990. One of her bathing suits (and its accompanying beach dress) is this leopard skin pattern gem.

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Image: Vogue

Leopard skin is an enduring classic. And when Diana wore it, it created an interesting contrast to her vast array of solid color swimwear. The leopard skin pattern says, “I’m here to have a good time,” and that’s exactly what Diana is doing. And as you can see, the gentle hues of brown and yellow, and the spots mesh flawlessly with the pristine white sand of the Bahamas beaches.

Flawless at the Parade

In 1989, Princess Diana attended a parade at the Dartmouth Naval College in Devon. Clad in a perfect red Catherine Walker dress and a Philip Somerville hat, you can see she’s turning naval heads left and right. For Diana, as well as for the navy men, the name of the game seems to be elegant suits, polished by light-colored buttons.

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Image: Insider

This outfit is a perfect example of Diana’s keen eye for clothing aesthetics: the dress, the hat, and the purse look as if they were made as a set. The blood-red color of the hat and dress work immaculately with the white trim and white buttons. And as her perfectly chosen outfit matches the prestigious uniforms of the navy, it’s almost as if she called in advance to coordinate!

Royal Shopping Spree

Of course, if Princess Diana went shopping with the goal of getting clothes that would look amazing on her, she would wear a stunningly elegant outfit while doing it. Here, the princess is photographed in 1994 on her way to shop at Harvey Nichols, in Knightsbridge.

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Image: Marie Claire

With her faint beige-bordering-on-white pants and matching turtleneck, her deep grey blazer, and stylish handbag, she looks like the ultimate elegant urbanite. Her golden earrings come together with her golden cuff buttons to form a subtle, but pleasing uniformity. Though clearly in possession of an outspoken fashion voice, workers from Diana’s favorite stores in the area have over the years reported that she was quite shy.

Spring Is in the Air

In this casual-leaning 1985 iteration of Diana’s fashion sense on display, she makes us all want to go out and buy a red cardigan ASAP. The soft white blouse lets the cardigan and the floral pants take center stage. The outfit screams “spring!” and makes us want to go for a nice stroll in the park on a sunny day.

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Image: Cosmopolitan

As many know, Princess Diana suffered from postpartum depression and in no small amount due to her volatile marriage. But through human connection and empowerment through fashion, she healed herself and did a great deal to try and heal the world. Even when her days were dark, her fashion was colorful and bright.

Breezy Dress for the Indian Sun

When Diana became princess (actually, even before), she dove headfirst into her royal duties. She traveled to dozens of countries around the world, cementing long-lasting connections with world leaders through her warmth and openness. When she arrived in India in 1992, she impressed everyone not only with her charm but also with her style.

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Image: Daily Express

In anticipation of India’s hot weather, the princess opted for a stunning, off-white, breezy dress. Under the dress, you can see her matching low heels. The whole thing comes together splendidly. To the surprise of some, Diana was perfectly at home mingling with the untouchables; the lowest echelon in India’s social caste system. This just shows that for Diana, humanity trumps all else.

A Ruby Among Onyx

In 1982, while pregnant with Prince William, Diana was pictured in an alluring red satin gown as she is arriving at the Barbican Center in London. Upon arrival at the gala performance, Diana and Charles were met by a delegation of officials. While the overwhelming majority in attendance were dressed in black tuxedos, Diana’s red dress offered a beacon of color and fun.

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Image: The Sun

The event, which was kicked-off by the queen the night before this picture was taken, was to celebrate the charity work done by the royals in helping struggling youth. When deciding what to wear, Diana was given a sketch of this dress by David Sassoon, and Diana scribbled the words “yes please” on the drawing. We can clearly see why. The red satin maternity gown certainly made Diana into a ruby among onyx.

Picture-Perfect on Easter Sunday

Here, we see the princess with her young son, Prince William, in 1992. They just attended an Easter ceremony, and now they are leaving with their eggs. For the occasion, Diana chose to wear a sleek pale yellow overcoat paired with a matching skirt with a navy hemline.

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Image: UK Home

The outfit was made by Catherine Walker – one of Princess Diana’s all-time favorite designers. The accessories, i.e. the close-fitting golden necklace and earrings, and the black and yellow hat, prettily match the color scheme of the outfit without competing for attention. And somehow, as if by coordination, Diana’s clothing matches the colors of the box of Easter eggs.

Scotland or France?

Diana was seen sporting one of her most sophisticated looks on a trip to Scotland with Prince Charles in 1981. Her debonair tartan outfit, designed by Caroline Charles, and her tasteful Stephen Jones beret have got her looking like a French painter, and it’s downright awesome. Not to mention her incidental upward gaze gives even more spice to the look.

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Image: The Scotsman

During the visit, the royals honored Scottish formal wear traditions. Prince Charles and Prince Andrew wore kilts for the occasion. Diana anticipated the dress requirements and chose an outfit with a plaid color scheme that paired with the plaid of the men’s’ kilts. Earlier that year, also in Scotland, Diana and Charles had their honeymoon, much of which was spent roaming around the beautiful and lush rolling hills in the countryside.

An Inspirational Photograph

In this picture, Diana is seen sitting on a bench in front of the Taj Mahal in India in 1992. Since India became independent from Britain in 1947, the two nations have maintained a close relationship, and the royals visited pretty frequently. Diana’s outfit here includes a red Catherine Walker blouse over a white shirt accompanied by an equally colorful purple skirt.

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Image: People

On the formality spectrum, the outfit is sitting snugly on that sweet spot between casual and official. In another picture of Diana on this bench, she is seen looking down at her shoes. Some time later, Christian Louboutin saw the photo and was struck like lightning by a bolt of inspiration. “She was looking at her feet, and I thought she looked so sad,” the world class shoe designer recalled years later. Thus the famous “Love” shoes were born.

Princess Picture-Perfect

This photograph is without a doubt one of Princess Di’s most ‘princessly’ looks she has ever pulled off. It was during an official visit to Newcastle, Australia, in 1983. This was on Diana and Charles’s first royal tour, and she dressed for the occasion in a vivid light pink Catherine Walker dress.

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Image: Glamour

At just 22 years old, Diana was already married, getting ready to have children, and totally immersed in her royal duties, including extensive worldwide travels. For part of their first trip, they were in Australia for about a month. It’s not just the majestic dress that makes Diana look like the quintessential princess, it’s the facial expression, and it’s the flowers at which she is delicately picking.

Irresistible for the Cameras

It’s well known that Diana was an exercise enthusiast, and this is one of her best sporty outfits ever. Her fashion sense was way ahead of her time, and this outfit would turn heads at any gym today. Her immaculate white attire includes a Harvard sweatshirt and white bicycle shorts.

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Image: Vogue

Though Diana did eventually grow accustomed to being under the gaze of the public eye, she particularly didn’t like being caught by the paparazzi on her way to and from the gym. It’s hard to blame the paparazzi though because she looks stunning in this outfit. Work or play, she always knocked it out of the park.

Gems in the Middle East

In 1989, Charles and Diana flew to the Middle East to visit the Gulf States and to visit British citizens in the region. A large part of their trip was spent dining and visiting with country leaders, including those of Kuwait and the United Arab Emirates. Of course, since these countries are so rich, the ceremonies and dinners were fastidiously luxurious events. But Diana was well prepared.

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Image: Glamour

For the trip, Diana selected some of the best of the best her wardrobe had to offer. In the spirit of luxury, for this event, Diana chose a Catherine Walker gown loaded with pearls, beads, crystals, and gold sequins. It had the effect of making her shine like a diamond. It was designed by David Emanuel and his wife at the time, Catherine. In fact, Emanuel’s claim to fame came when he designed a dress for Diana back in 1981.

Mismatching and Breathtaking

This is Diana at her rebellious best. She was a pro at breaking tradition in the most stylish possible way. Whereas most of the royals usually went for the safe route, Diana had no problem wearing strapless gowns of all sorts. And this is one of her greatest fashion triumphs.

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Image: Vanity Fair

For attending the America’s Cup Ball in London in 1986, she went for a stunning strapless Murray Arbeid flamenco, complete with a black choker and mismatched red and black gloves. In contrast with most royals, Diana was also not afraid to wear black at other events than a funeral. And her daring outfits certainly paid off.

Making a Difference, in Style

On her trip to Bosnia in 1997, Diana was full of smiles and styles. But instead of extravagant gowns and lavish dresses, on this trip, Diana leaned more towards jeans and blouses. And this look is classic Princess Di. The white blouse, slightly opened at the top, flows organically into her light blue jeans. It’s all held in place by a light brown leather belt.

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Image: The Daily Telegraph

Matching her style to any audience and destination anywhere in the world was one of Diana’s specialties. On this trip, Bosnia was still in bad shape after the conflict there in the mid-1990s. The nation was not in the mood to party. Diana’s visit was more of humanitarian concern, and her outfits reflect the friendly and “let’s get to work on fixing stuff” sentiment she expressed while in the region.

Gingham in the Far East

The photos of Diana on her a state trip to Thailand in 1988 prove to us that she also could have pursued a career in modeling. After a red carpet greeting with the Thai monarchy, and after the princes inspected a Thai military unit, the royals were brought on a tour of an umbrella factory. Diana wore a gingham shirt and bright white Alistair Blair skirt, perfect clothes for the warm tropical climate.

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Image: Vogue

The thin black leather belt is the perfect little cherry on top of Diana’s elegant attire. During their visit, King Bhumibol Adulyadej’s, Diana and Charles’ host celebrated the sixtieth anniversary of his accession to the throne. The Thai leadership knows a thing or two dressing well – the Thai monarchy has been around for 750 years!

Friends and Angels

Princess Diana had a long and close relationship with Mother Teresa, which they developed through their vast shared involvement in charity and advocacy. They maintained their close relationship until their last days. Mother Teresa passed away from natural causes less than a week after Diana’s untimely death.

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Image: Daily Mail

For their second meeting in 1992, Diana wore an angel white full-sleeved jacket paired with an equally beaming skirt. As you can see, Diana’s attire perfectly matched the subtle traditional grabs of the nuns. The solid white design gives off a message of compassion and peace, almost like a dove.

Classic Sloane Ranger

In this priceless early 1980s shot of the princess, we see her doing total justice to an awesome Sloane Ranger outfit. The official definition of this style is “…a uniform, effortless, and unambitious although sophisticated [look].” Diana captures this essence. She’s wearing a slightly wooly bright white cardigan over a cerulean shirt.

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Image: Daily Mail

Her pitch-black skirt contrasts nicely with the cardigan and lets it keep center stage. The pearl necklace and the close-fitting handkerchief around the neck, along with the emerald earrings quietly work to add accentuating detail to this already-fantastic outfit.

Perfect Stripes and Solids

This is the look of a 20th/21st century British royal. It’s highly reminiscent of the outfits we see Queen Elizabeth wear all the time. At the collar lapel and cuffs, Diana’s long purple jacket inverts and gives way to its striped black and white interior. Though seemingly oceans apart, the stripes and solids blend fabulously.

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Image: The Daily Telegraph

The princess’s 1985 Christmas day attire was topped off by a matching hat with dark black trim. From what we know of Diana’s style and her fearlessness when it came to form-fitting dresses and open shoulders, this might not have been her favorite outfit. Although, outfits like this one were ubiquitous in her wardrobe, as the style was a staple of the royal fashion scene.

Dashing In Black and Yellow With the Troops

In this 1985 photograph, we see the princess wearing a tracksuit and smiling away. It was taken while she was visiting the Royal Hampshire Regiment’s Wavell Barracks in Berlin, Germany. Following WWII, Britain installed several divisions in Germany, and the numbers grew during the Cold War. Visiting those troops was a usual trip for the royals.

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Image: Cosmopolitan

Diana was perfectly dressed for the occasion. The weather was grey and the morning was chilly. Visiting the troops requires climbing on, in, and out of all sorts of military equipment and vehicles, so she needed a flexible outfit. Her tracksuit was mostly black but stripped by a thick yellow pass on the stomach and hood areas and a thinner yellow streak on the pants.

Life of the Party in Sequined Blue

Here we see a young Diana and Charles attending a party at the Royal Academy in 1981; two years before their marriage. At this time, Diana was not yet the princess, her title was “Lady Diana Spencer.” For the festive occasion, she chose a midnight blue dress adorned with bright sequins.

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Image: Vogue

In 1981, Diana still had a reputation for being shy, and many have noted that her facial expression in this picture embodies that shyness. But even in these early years, she went against the grain and empowered herself through fashion. Contrary to the grand but somewhat rigid style of royals at the time, the dress Diana chose had completely open shoulders and thin spaghetti straps.

Splendid in the Garden in Pink and White

Leaning against a sundial in the yard of her home at Highgrove House in the 1980s, we see Diana in one of her natural habitats. No state dinners, no diplomatic mission, just the princess hanging out. She and Charles decided to let a camera crew come in and take pictures so the public could catch a glimpse of the royal couple’s daily lives.

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Image: Yahoo

In this photograph, Diana is pictured in a happy thin pink and white striped collared shirt. And she chose to go with fresh white coveralls that match her low cut white shoes. As always, Diana’s outfit is in perfect synchrony with her smile, her hair, and her jewelry. Not to mention, being photographed and/or filmed on a daily basis is tiring, but by the mid-1980s, Diana had already nailed the perfect poses.

A Dress to End All Dresses

“[The dress] had to be something that was going to go down in history, but also something that Diana loved,” explained David and Elizabeth Emanuel, the designers of Diana’s 1981 wedding dress. And go down in history it certainly did; worth about $600,000, it’s one of the most famous dresses in the world and one of the fashion industry’s most closely kept secrets.

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Image: Forbes

The historic dress featured an antique lace gown and a ivory silk taffeta. The train trailed behind the princess for about 25 feet. Throughout, the dress was lavishly embroidered with pearls and sequins. The whole world gave the dress positive reviews. A few people disagreed, however. One said that it’s “too much dress, too little princess.” But we think it’s just right! The grandiosity of the dress matches Diana’s monumental status.

The Revenge Dress

By 1994, the princess was no longer “shy Di.” By then, she had fully embraced her status as a fashion luminary and her outfits grew increasingly bold and stylish. Some people have called this gown the “Revenge Dress.” Designed by Christina Stambolian, the Revenge Dress was open at the shoulders, with the straps threatening to slip further and further down, and it looks absolutely spectacular.

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Image: Insider

The multi-lane pearl necklace beautifully wraps around her neck and is held together by a large jet black stone in the middle. But how did the dress get its name? Well, the same night that Diana attended a party at the Serpentine Gallery, a documentary came out detailing Prince Charles’s infidelity with Camilla (now Duchess of Cornwall). This is maybe why Diana’s fashion message was extra bold that night.

Puffy Perfection in Austria

Rain, shine, wind, or snow, Diana’s fashion sense always impressed us and the rest of the world. Spotted walking around Lech, Austria, while there on a ski holiday in 1994, she wore a super cool red puffer jacket. She paired the puffer with dark grey leggings, pulling off a superb warm-but-comfy look.

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Image: Vogue

Under the red puffer, she is wearing one of her favorite kinds of clothing ever: the turtleneck. Diana was relentlessly pursued by paparazzi and tabloids, so in an attempt to avoid detection, she often wore a baseball cap and sunglasses. Honestly, though, this just made her look even cooler and further enticed the media.

Bringing Back Polka Dots

At Nicholas Soames’s wedding in Westminster, London, in 1981, the royal ladies are looking classic. No open shoulders or spaghetti straps in sight for this one. Diana wore a charming red maxi polka dot dress made from silk. And she had a matching red hat that veered upward near the back of the head.

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Image: The Daily Telegraph

Among the white dots on the solid red, Diana’s dress also had little blue and green flowers. To go with the matching dress and hat, Diana also brought along a red handbag with white trim. This is early Diana, and she still is in the experimental stages of her fashion journey. At this point, she still hasn’t quite grown comfortable with breaking from the royal norms.

Looking Great in the Minefield

In 1997 (the year of her tragic death), Diana was the most famous woman in the world. By now she had seen it all; affairs, two kids, diplomacy, depression, philanthropy, global travels, fashion trailblazing, and more. Still, she surprised the world when on a trip to Angola, she took a daring walk across a minefield. This was following her international call to ban the use of mines.

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Image: BBC

Her trip is largely credited with doing a lot to advance the ban. So, we know Diana looks great at prestigious events or when she’s casual, but as you can see, she also looks amazing in the middle of a once-war zone. Under her protective gear, she wore light beige pants and her signature white shirt. Minimalistic, elegant, and beautiful. She chose light brown shoes and she wore golden earrings and a golden bracelet.

Faultless at the Film Fest in Chiffon Blue

Diana wore a dreamy chiffon blue ballgown to the 1987 Cannes Film Festival. The dress was designed by one of Diana’s favorites, the tried and true Catherine Walker. This was early days for the princess and she still was not as outspoken as she would come to be later in life. The image she gave off here was one of a fairytale princess. And this outfit definitely suited that persona.

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Image: Vanity Fair

The open shoulder design was slightly softened by the fabric around the neck, giving the whole ensemble parsimonious flowing energy. Her jewelry was also spot on. The sapphire blue earrings, ring, and necklace added just the right finishing touches to Diana’s evening wear as she attended one of the most esteemed events in the film industry.

Feline Vacay Wear

A couple of months before her heartbreaking passing in 1997, Diana traveled to St. Tropez in southern France for a holiday. Her tumultuous marriage with Prince Charles ended in divorce about a year earlier. Weeks before this photograph was taken, Diana and film producer Dodi Fayed, whom she visited during this trip, had begun a romantic relationship. Sadly, he was in the car and also passed away in the fatal car crash that year.

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Image: Vogue

It’s hard to remember Diana without acknowledging that she looked prepossessing wherever she went. As seen on other vacations as well, here she is decked out in a feline print one piece. This one features a combination of leopard, cheetah, and tiger print, making it uniquely voguish.

The Royal Look

This photograph of Princess Diana, Queen Elizabeth, and Prince Charles was taken in 1981, the year of Diana and Charles’s wedding. Though the queen and the princess to be’s outfits do have some differences, they are very, very similar. Diana’s color scheme is navy blue with a white collar and a bright red bow in the middle. Princes Charles, as always, is looking sharp in a tailor-made suit.

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Image: The Sun

In contrast, the queen’s sky blue dress is monochromatic, including the bow. Both ladies are wearing pearl necklaces, giving the clothing a little extra shine. Standing in Buckingham palace all looking sharp, the trio embodies the spirit of 21st-century royalty. It was years later revealed that Diana was underwhelmed by Charles’s proposal. She thought it was a little lackluster and not as romantic as it could have been.

Princess of Wales, Queen of Denim

This is 100% classic Princess Diana out shopping. She paired a cozy turtleneck (floral in a very minimal way), with a pair of tapered and slightly bleached mom jeans from Topshop. The sweater has that nice vintage vibe and certainly looks very comfortable for a chilly day out and about. It’s pics like these that made Diana go down in the history of streetwear.

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Image: Insider

This photo was taken in 1992, and though you can’t see his face, young Prince William is there trailing behind her. Throughout history, royalty tended to leave a lot of the hands-on parenting duties to nannies and other service people. But Diana went against that centuries-old pattern, and became the epitome of royal hand-on parenting. Some have said that she set the precedent for Kate Middleton and Meghan Markle.

Lighting up the Premiere in Taffeta

The princess showed up with this dashing dress at the premiere of When The Whales Came, in 1989. She looked immaculate in this Catherine Walker bois de rose taffeta strapless. It lit up the red carpet with a soft blue floral design and sassy sleeveless vibe.

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Image: The Daily Telegraph

As Glamour aptly put it, “[this dress] may have pushed the parameters of what the Buckingham Palace style guide allowed.” Already a part of the royal family for years now, Diana garnered tremendous media attention wherever she went. Though overwhelming at times, she excelled at it.

Favorite Threads for the Middle East

On her last day in Cairo on her 1992 visit to Egypt, Diana visited the Commonwealth war cemetery in Heliopolis. Refined as always, she wore a white and cadet blue suit made by Catherine Walker. It was accompanied by a Philip Somerville hat with an identical color pattern.

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Image: Yahoo

This was one of many Catherine Walker dresses that filled the princess’s wardrobe. In total, the legendary fashion designer would go on to make over 1,000 clothing items for the princess, including the dress in which she was buried. Walker passed away in 2010 at the age of 65 due to health complications, but she and Diana left behind her legacy of royal fashion.

Sweater Ain’t So Ugly Anymore

The one is vintage Princess Di all the way. She and Charles are seen here in 1981 during their honeymoon in Scotland. Though she did enjoy much of it, she opened up about the experience in a book entitled Diana: Her True Story – in Her Own Words by Andrew Morton. She said, “There are so many negative atmospheres. That house [the estate in Scotland] sucks one dry.”

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Image: Time

Negative experiences notwithstanding, she brought new fashion spice into that place that no one had ever tasted. Somehow, she managed to make huge rainboots, baggy khakis, an almost-ugly sweater, and a fresh white turtleneck magically coalesce into an outfit that pleases the eyes. We would never think to try and combine these (we’d probably fail), but Diana had a keen appreciation for style and made it work wonders for her.

Turning Heads at Tea Time

During Charles and Diana’s official visit to Japan in 1986, the princess partook in a customary Japanese tea ceremony Shugakuin Imperial Villa gardens in Kyoto. She wore a peach pink kimono decorated with a variety of flowers, cherry blossoms, and dragons. And although you can only tell by her sleeve, under the kimono she showed up the ceremony with a white dress spangled with bright red circles.

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Image: The Daily Telegraph

Upon her arrival, to the ceremonial grounds Diana was greeted by Japanese officials who escorted her to a display of kimonos that she was instructed to choose from. The one she is wearing in this picture is worth about $50,000! True, carrying out the extensive duties expected of a princess is not easy, but it has its moments.

Pearls and Open Sky at the Ballet

In this 1992 shot, we get to see the outfit Princess Diana wore to the gala event for the London City Ballet. Once again, she’s dressed in a dress courtesy of Catherine Walker. The bottom half is reminiscent of the one she wore to the Cannes Film Festival: flowing gentle blue. The top half, however, is intricately embroidered with shiny sequins.

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Image: Business Insider

The one of a kind Catherine Walker dress is estimated to now be worth between $80,000 and $100,000. From 1986 to 1996 (when the company closed) Diana was a frequent patron at the ballet. For ten straight years, through her social aptitude and connections, she raised money for the ballet, one gala and one perfect outfit at a time.

Denim and Varsity Solids in the Endzone

This all-out fashion win has got us confusing Princess Diana for an American college football player. Pictured in 1992, she’s got fairly short hair, blue jeans, and a traditional black and red varsity jacket. Under the jacket, she’s wearing an ink-black shirt.

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Image: Time

Except for some small gold-colored designs around the pocket area of her jeans, and the red and black striped trimming of the coat, the outfit is all solids, and it looks great. Versatility and diversity were two of the foundational pillars of Diana’s fashion revolution. One day she could be in at a red carpet event wearing a shoulderless dress, and the next morning she could be shopping in Knightsbridge, clad in denim.

Smashing and Dashing on U.S. Soil

This authoritative off-the-shoulder dress, made by legendary designer Victor Edelstein, came to be known as the “Travolta Dress” for pretty obvious reasons. It’s hard to tell by the picture, but it’s not black, it’s dark midnight blue. With the help of the daring dress, Diana stole the show at gala dinner at the Whitehouse in 1985.

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Image: People

There were a few famous actors invited to the gala event that night. Legend has it that Diana actually came to the event with her heart set on dancing with a superstar. She ended up dancing with John Travolta after he asked her at the urging of Nancy Reagan, but she later recounted that who she really wanted to dance with was Mikhail Baryshnikov.

Diana’s Trusty Pals

For over 15 years, superstar designer Catherine Walker was the right-hand woman for Diana when it came to fashion. But Philip Somerville is a good contender for her right-hand man. Her dresses and suits and his hats are a match made in style heaven.

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Image: The Daily Telegraph

Some commentators and fans have even gone as far as to say that Somerville helped in large part form Diana’s fashion taste, and in turn, the entire country’s. This winning combo features a long yellowish, cream-colored with a matching suit shirt. The collar and the buttons are light and gentle pink and they pair up gorgeously with the pink hat.

Virgin Atlantic Is Pretty Fly

Without a doubt, Diana liked to have fun with sweaters. Here, in 1995 she was photographed leaving the Chelsea Sports Club after a workout. On this casual occasion, she wore a comfy-looking Virgin Fly-Atlantic sweater. You might think so beforehand, but it goes really well with the neon orange bicycle shorts.

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Image: Vogue

This particular sweater had quite a history. It was given to Diana by the founder of Virgin Atlantic, and then later it was given by Diana to her trainer, who later put it up for auction and used the proceeds to help a Malawian family based in South Africa. Interestingly, Diana always wore this sweater in an attempt to resist paparazzi overtures: if you’re a celeb and they catch you with the same clothes, they can’t run the pictures.

Coolest Gal at the Cocktail

Dressed in another stunning Catherine Walker classic, Diana attended an event in the United States in 1997 just a couple of months before her accident. She’s looking just as sharp and pretty as ever. The cocktail dress features subtle red and grey florals against a background of pristine white.

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Image: Vogue

It was the best choice for the occasion, as it teeters on the fence between formal, casual, and party. It’s a little daring, and it looks downright amazing on her. By the year 1997, Di wasn’t shy. She seized the reigns of power through charm and style and became one of the most fabled fashionistas to ever walk the earth.

Lady in Red

The eye-catching princess is pictured here leaving the hospital after the birth of her second son, Prince Harry. She’s holding him in her arms and looking very happy in 1984. Diana made a bold statement here in her bright red coat, designed by Jan van Velden, and, of course, matched it with very cute pumps in the same shade.

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Image: Us Weekly

This outfit’s magic is all in the details – from the red and white striped shirt to the red scarf, it really is a winner. The cute red and white bows on the pumps really seal the deal for us and complete the ensemble. Who knew red and white went together so well (except for Canada)?

Flattering at the Polo Match

Diana really loved sports. A few times, she showed up at her sons’ school during track and field and with some other parents, participated in the activities. She was always seen smiling away and going to and from the gym.

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Image: Vogue

Here, Diana attended a polo match in 1983. She wore a crisp white bow blouse (a style she had perfected even years prior) and light blue seersucker pants. To finish off the regalia, she wore an elaborately colored floral purse, gold earrings, and light brown aviators. For a sunny day and polo, this outfit is a total winner.

Momma and Two Royal Boys

Nothing says sunny days like this look. Diana is pictured here with her two sons, clearly during summer. Prince Harry and Prince William are of course dressed in matching red and white outfits. William is wearing a classic striped shirt, and Harry is in a red shirt with pink overalls. Could that be any cuter?

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Image: Daily Express

Diana herself is matching yellow and gold and looking ever so summery. We personally adore the big gold earrings and the gold watch. She really has a way of matching things without it feeling forced. An elegant and casual outfit at the same time, perfect for the easy-going British summer.

Carving Up the Mountain and Looking Debonair

In this photograph, we see Princess Diana and little Prince William looking chic on the ski hill. These days, now that they’re all grown up, it’s no secret that both princes are avid ski vacationers. This is where it all started, back in 1991. Diana is wearing a smooth uniform red ski suit.

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Image: Daily Mirror

The white snow and the shining sun are reflecting off of the suit’s leathery material. Complementing the suit nicely, Diana decided on elegant black and white color schemes for her ski boots and her poles. Her gloves are solid white. Even when she’s vacationing (or maybe especially), she firmly placed herself at the forefront of fashion.

Momma’s Got Mad Style

Here we see 20-year-old and nine-month pregnant Princess Diana in 1981. Even when she was very pregnant she was out and about, charming everyone and performing her fast-paced royal duties. When you’re this pregnant, the name of the game in comfort. But for Diana, it’s also style.

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Image: Glamour

At a polo match, she wore a pink airy, breezy, and elegant maternity gown. Like other outfits of hers, the gown is stepping off and then back onto edge between casual and formal. She makes comfortable look elegant like no one else. To top it off, she chose white slippers.

Ball Gown in Aussie Town

This photograph was taken in 1985 during a royal visit to Australia. At a formal event in Melbourne, Diana is illuminating the dance floor while wearing a lovely teal off-the-shoulder ball gown. For jewelry, she wore a ravishing encrusted white headpiece and matching earrings.

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Image: Vogue

The bodice of the dress, somewhat close-fitting, is topped off with an adorable bow on the shoulder. Under the bodice, the dress flows freely. Diana was strong, and though she had periods of struggle, she set the golden standards for princesses for generations to come.

Matching Prince and Princess

In many photographs, we see Diana dressed up in one of her thousands of perfect outfits, and then we see the little princes wearing sleek suits with little child-sized ties. It’s cute. But here, they’re matching. Diana is wearing a long pale blue Catherine Walker coat with white trim and a hat of matching colors.

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Image: The Daily Telegraph

The coat parts ways at the top and gives way to a snow-white handkerchief. To top it all off, she wore white gloves. She dressed little Prince William in a matching one-to-one coat. It’s extremely cute. True, William didn’t have the gloves or hat, but other than that, he looks like Diana’s little twin.