Our Favourite Looks: Princess Diana Outfits

Taking a Look at Princess Diana’s Best Fashion Moments

While virtually every woman that has walked the halls of Buckingham Palace throughout recent years has influenced fashion in their own ways, no one has come quite as close to the lasting legacy left behind by Princess Diana. 

Remembered for far more than just her clothing, the People’s Princess was unique for using her fashion to communicate with those around her. 

Despite countless trends having come and gone in the past decades, Princess Diana continues to reign as a style icon in her own right thanks to her simultaneously timeless yet daring style that set herself apart from other royals and is perhaps the most influential fashion icon of the 20th century whose reach extends to today.

Nearly 25 years since her tragic death, we still see bits and pieces of Princess Diana evoked in modern trends, with many young people taking inspiration from her outfits from over 30 years ago. 

Let’s take a look at some of Princess Diana’s best fashion moments that we still think about today.

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How Was Princess Diana a Fashion Icon?

After Princess Diana and Prince Charles’ wedding day in 1981, Diana, Princess of Wales would embark on a series of public appearances and royal tour after tour for the rest of her life, with a multitude of ensembles and dresses to suit the different occasions she would attend. 

While this is the same for all royals, what set Princess Diana apart was how much of her personality was found in her style, and how this would evolve with the different phases of the late princess’s life.

Even outside of special events, Princess Diana’s style on the street would have a huge impact on commoner fashion, something unique to her and that brought her closer to the public that admired her. This level of casualness from the royal family was never before seen, and this element of style brought in by Princess Diana would later be taken inspiration from by her daughters-in-law, Kate Middleton and Meghan Markle.

Who Styled Princess Diana?

While everything Princess Diana wore had much of her own input and abided by her own fashion rules, Anna Harvey’s assistance as her stylist and fashion mentor during her marriage to Prince Charles and subsequent divorce was the key factor that would turn Lady Diana Spencer into an international style icon.

Additionally, while Princess Diana would sport several different designers throughout her life, perhaps the most notable designer partnership she maintained throughout her career was with Catherine Walker, who delivered many of Princess Diana’s best fashion moments, with many a red Catherine Walker dress or polka dot dress being spotted at different occasions.

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Princess Diana’s Best Fashion Moments

The Engagement Suit

While Princess Diana’s best fashion moments in the future would be meticulously decided upon by her stylist before every event she would attend, the outfit that Princess Diana would be introduced to the world in, and that would be considered one of her most memorable garbs, was picked off of a Harrods rack by Lady Diana Spencer herself. 

The blue dress, or rather skirt suit, was hurriedly bought after Princess Diana was turned away from high-end boutique, Bellville Sassoon, by a sales assistant who didn’t recognise the soon-to-be Princess of Wales. However, this mistake would end up being quite fortunate, as the suit’s strikingly blue tone would end up complimenting her sapphire engagement ring quite beautifully.

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The Splendours of the Gonzagas Dress

Before the iconic period of her sleek and sophisticated evening dresses, the style Princess Diana adopted in the earlier years consisted of youthful layers and ruffles, as best seen in this Bellville Sassoon gown. 

The princess arrived at the Victoria and Albert Museum wearing this ethereal piece, a dreamy off-the-shoulder chiffon ball gown with a matching choker.

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The Christening Dress

At Prince William’s christening in 1982, Princess Diana wore a simple dress and matching hat, very much the typical attire expected of the royals while still imbuing it with her own personality and style. 

The lively pink floral dress, partnered with a matching pink hat, would be seen again the following year during a tour of Australia’s Sydney Opera House.

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The Travolta Dress

This midnight blue velvet dress designed by Victor Edelstein would become well-known around the globe when photographs and footage of Princess Diana dancing in it with a young John Travolta were released. 

The princess wore the dress to a 1985 gala dinner at the White House after spotting a burgundy version of it in the designer’s studio and requesting the beautiful custom colour.

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The Pink Versace Suit

Pink was well-known to be a favourite colour of Princess Diana, and the Princess of Wales would often be seen at different functions wearing varying shades of the vibrant hue. 

This particular set was designed by Gianni Versace and inspired heavily by American First Lady Jackie Kennedy, with a matching hat to pair with it by Phillip Sommerville.

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Princess Diana’s Wedding Dress

Perhaps one of the first dresses that come to mind when thinking of Princess Diana, the opulent ivory silk taffeta and antique lace wedding dress that was seen in its full glory on the steps of St. Paul’s Cathedral, with Lady Diana Spencer on her way to marry Prince Charles sparked a huge trend of large, poofy wedding gowns through the rest of the 1980s. 

Designed by David and Elizabeth Emanuel, Princess Diana’s wedding day dress featured a 7-metre long train — the longest in royal wedding history. 

The wedding dress was also so closely guarded before its reveal that a backup design was created in the case the original was leaked. Luckily, it wasn’t, and both the wedding dress and wedding day went down as arguably some of the most iconic moments in recent history.

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The Cannes Dress

In 1987, Princess Diana and Prince Charles attended the Cannes Film Festival for its 40th anniversary. Princess Diana wore a powder blue chiffon gown by one of her favourite designers, Catherine Walker. 

The princess paired the dress with a matching scarf that draped from her neck and down her back. The number would, later on, be sold at auction for £81,000 in 2013 with the proceeds going to a children’s charity.

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The Pink Gingham Trousers

Another article in the colour of choice of Princess Diana, this casual outfit of pink gingham trousers and a matching pink jumper was spotted when Princess Diana, Prince Charles, and their children spent some family time in Highgrove in 1986. 

In pictures snapped with a young Prince Harry, we see one of Princess Diana’s best fashion moments for the modern casual-preppy look which continues to be a sought after look decades later.

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The Uptown Girl Dress

In 1985 at the Royal Opera House, Princess Diana surprised Prince Charles and their VIP audience by taking the stage with dancer Wayne Sleep and performing a dance to ‘Uptown Girl.’ The performance, which was only brought to the public’s attention 10 years later when the tabloids got their hands on official photographs taken by the Royal Opera House, had found Diana wearing a beautiful satin piece. 

The white dress Princess Diana wore on the evening was simple but left an impression on many viewers thanks to the flowiness of its skirt and how it hugged the princess’s statuesque figure. While the dance may not have been recorded at the time, the television series The Crown recreates the dance as well as one of the more obscure of Princess Diana’s best fashion moments for the modern public to witness.

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The Maternity Coat

At the announcement of her pregnancy with Prince William and at subsequent outdoor gatherings until his birth, Princess Diana sported different variations of a vibrant and loose coat over her maternity dress, both of which still kept with her signature style. 

This Bellville Sassoon maternity coat that Diana wore to an event in Huddersfield is a sweet reminder of that series of fashion moments in her favourite colour and is considered as one of Princess Diana’s best fashion moments while she was pregnant.

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The Post-Pregnancy Dress

The fashion press was surprised to find Princess Diana wearing this blue dress out and about at an event just months after giving birth to the newborn Prince William. 

The dress, designed by Bruce Oldfield, was a dramatic return to the world of public affairs for Princess Diana, with its bright blue colour, striking circle pattern, draping silhouette, and ruffled off-shoulder detail.

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The Off-Duty Outfit

While there are countless photos of Princess Diana wearing glamorous gowns, cocktail dresses, and high heels, as she accompanied Princes Charles at events, the Princess of Wales also became a street style inspiration in her downtime. 

Walking the streets of London or out and about at outdoor events like a polo match, the influences of Princess Diana’s casual attire can still be spotted today, with her athleisure looks of baggy sweaters over cycling shorts and chunky trainers with sunglasses worn being particularly in fashion, with many around the globe and in London wearing the very outfit Princess Diana can be seen wearing here in the 2020s.

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The Elvis Dress

Another Catherine Walker dress, the Elvis Dress was embroidered with over 20,000 pearls and commissioned by Princess Diana for an official trip to Hong Kong, with the pearls being a popular symbol of the Orient. 

The dress garnered its nickname from its accompanying bolero with its upturned collar reminiscent of the style of the King of Rock.

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The Swan Lake Dress

The post-divorce wardrobe of the Princess of Wales included many short cocktail dresses that accentuated her figure and that would become staples in the 1990s. 

This sparkling, ice blue shift dress by Jacques Azagury that Princess Diana wore to an English National Ballet performance of Swan Lake at the Royal Albert Hall is a timeless favourite, accompanied by beautiful matching accessories and an unforgettable diamond necklace by Garrard.

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The Serpentine Dress

Another example of the short style Princess Diana would opt for after separating from Prince Charles, this one by one of her favourite designers, Catherine Walker, is a grey dress that Princess Diana wore to the Serpentine Gallery in London in 1995 features a halter neck and beaded all-over details, a dress that would still fully be worn and in fashion decades since Princess Diana first wore it.

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The Pretty in Pink Dress

During a royal tour with Prince Charles to Australia and New Zealand in 1983, Princess Diana captured hearts in Brisbane while wearing a candy pink gown by Victor Edelstein partnered with the Spencer family tiara adorned on her head. 

The press captured Princess Diana wearing the lovely piece partnered with accessories of sapphire and diamond gifted to her by the Prince of Saudi Arabia.

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The Revenge Dress

We would be remiss not to include the dress that caused a flurry all over the world. On the night Prince Charles admitted his affair with Camilla Parker-Bowles to the world in 1994, Princess Diana confidently strode into the Serpentine Gallery for a fundraising dinner wearing an off-the-shoulder black silk dress with a sweetheart neckline designed by Christina Stambolian. 

The dress that Princess Diana donned would be described as the “I’ll Show You Dress,” “Serpentine Cocktail,” and “Revenge Dress,” among other nicknames, became a headline in every paper, overshadowing the confession made by Prince Charles. 

The dress, which has since become perhaps the most famous dress Princess Diana has ever worn, was nearly set aside before the events of the day transpired. Designed three years prior, the dress was deemed too risque. But stylist Anna Harvey would reveal that Princess Diana would change her mind at the last minute, wanting to “look a million dollars.”

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Final Note

From a youthful ballgown to a tweed suit, a polka dot dress and matching hat to a yellow dress and matching shoes, a short red shift dress to a puff-sleeved blouse, or a red jacket with a black bow tie to a beautiful flowing purple dress, there are more than just a handful of unforgettable looks that Princess Diana wore throughout the years and that each of us remembers fondly and that continue to inspire us.

A fashion icon from the moment she was introduced to the public, Princess Diana remained so even after leaving Prince Charles and her duties for Buckingham Palace behind and as she continued her humanitarian tours around the world in her own time. 

We watched as her fashion evolved from frilly gowns to chic shift dresses, and even witnessed her influence the fashion world as did fieldwork in foreign countries or as she stepped out in jeans and jumpers to spend time with young Prince William and Prince Harry. 

No matter how many years or trends pass, it’s certain that Lady Diana Spencer will forever remain an inspiration for many in fashion and beyond.