IE 11 is not supported. For an optimal experience visit our site on another browser.

Princess Diana's best fashion moments through the years

From her wedding dress to the oversized crewneck and bike shorts, Princess Diana's fashion sense still has a strong grip on all of us.
Over the years, and even after her death, Princess Diana has proven herself to be a perpetual fashion icon.
Over the years, and even after her death, Princess Diana has proven herself to be a perpetual fashion icon.Johnny Eggitt / Tim Graham / Jayne Fincher / Getty Images

The People’s Princess had many celebrated style moments — and is still recognized as one of the greatest fashion influences of our time.

Diana Spencer, born in 1961, went on to marry the heir to the British throne (Prince Charles) and touched the hearts of people around the world with her personality, her humanitarian efforts and of course, her impeccable sense of personal style. 

Her style transcends the decades she lived through as a royal, and some of her most influential outfits continue to inspire others. From her horseback riding/blazer look to her revenge dress, here are some pictures of Princess Diana that prove her sartorial influence lives on.

1983: Brisbane

Princess Diana truly epitomizes a princess in this darling Victor Edelstein dress. Accompanying her dress is a tiara, and matching sapphire earrings, necklace, bracelet and of course, her notable sapphire engagement ring, which she replaced post-divorce for an aquamarine bauble.

Diana In Brisbane
The Princess of Wales wears a pink Victor Edelstein dress and the Spencer tiara to a state reception in Brisbane, 11th April 1983.Jayne Fincher / Getty Images

Prince William also proposed to Kate Middleton with the exact sapphire engagement ring Princess Diana once wore.Bangkok: 1988

In this look, Princess Diana sports a gorgeous cerulean belt (someone ring Miranda Priestly's line ASAP) with a flattering white skirt and a flutter-sleeved top. And if we know anything about Princess Di, it's that she'll be debuting her outfits with a classic kitten heel or pump to match.

Charles and Diana In Thailand
Charles and Diana, Prince and Princess of Wales, during their official visit to Bangkok on February 5, 1988 in Bangkok, Thailand. Georges De Keerle / Getty Images

James Bond movie premiere: 1985

Diana in a floor-length golden gown designed by Bruce Oldfield. Need we say more?

Diana At Bond Premiere
Princess Diana arrives for the London premiere of the James Bond film "A View To A Kill" at the Empire, Leicester Square, July 1985. She is wearing a gold lame evening gown by Bruce Oldfield. Jayne Fincher / Getty Images

Birmingham Airport: 1984

If common people saw someone dressed on a plane like this in the 21st century, they might look on with confusion. But, of course, Diana was a royal, so there were to be no sweatpants on an airplane (or, anywhere, really) for her. Nevertheless, she looks prim and perfect in this long Catherine Walker red coat with black trimming and a hat to match.

Diana In Birmingham
Diana wearing a red Catherine Walker coat and a hat by John Boyd upon her arrival at Birmingham airport, England, February 1984. Jayne Fincher / Getty Images

Switzerland: 1988

Diana took après-ski to the next level with this glam wintery look.

Diana In Klosters
British royal Diana, Princess of Wales (1961-1967) wearing mirrored sunglasses during a holiday at the ski resort of Klosters, Switzerland, 9th March 1988. Princess Diana Archive / Getty Images

New York: 1997

This photo, taken a mere two months before Princess Diana was killed in a car crash, exemplifies a perfect storm of royal, yet casual, glam. Her dress is by one of her most worn designers, Catherine Walker, and the shoes are Jimmy Choo.

Diana In Dress By Catherine Walker
Diana, Princess Of Wales Arriving For The Christies Party In New York Wearing A Champagne Coloured Dress Designed By Fashion Designer Catherine Walker. Her Shoes Are Designed By Jimmy Choo. Tim Graham / Getty Images

Scotland: 1981

This photo, taken sometime before Princess Diana and Prince Charles were to be married, shows Diana's more casual side. Her printed sweater, the turtleneck and the pleated pants all are examples of trends that continue to recycle themselves through the years — further proving Princess Di was ahead of her time.

Prince Charles, Prince of Wales with his fiance Lady Diana S
Prince Charles, Prince of Wales with his fiance Lady Diana Spencer during a photocall before their wedding while staying at Craigowan Lodge on the Balmoral Estate in Scotland.Tim Graham / Getty Images

Windsor: 1983

Two words: sheep. sweater.

We're wondering not only how we could copy Princess Diana's look, but also Duchess of York Sarah Ferguson's. This image was taken at the Guard's Polo Club in Windsor.

Warm And Wonderful
Diana with Sarah Ferguson at the Guard's Polo Club, Windsor, June 1983. The Princess is wearing a jumper with a sheep motif from the London shop, Warm And Wonderful.Georges De Keerle / Getty Images

Mallorca: 1988

Did Princess Diana start #hotgirlsummer unknowingly?

In this image, she wears a floral patterned strapless bikini, with a matching sarong for the bathing suit in her hand — and, to everyone's envy, is on a yacht in Mallorca.

In memory of Diana, Princess of Wales, who was killed in an automobile accident in Paris, France on August 31, 1997.
Diana, Princess of Wales, wearing a patterned bikini and holding a matching sarong, stands on board a yacht, whilst on holiday on August 16, 1988 in Majorca, Spain.Anwar Hussein / WireImage

Scotland, 1981

In this ever-so-chic look, Diana sports an orange tartan dress, complete with a "tammie" cap (a traditional Scottish-style hat.)

Diana In Scotland
Diana, Princess of Wales, wearing a tartan dress designed by Caroline Charles and a black Tam o' shanter style hat, attends the Braemar Highland Games on September 05, 1981 in Braemar, Scotland. Anwar Hussein / WireImage

United Kingdom: 1984

What do you wear when a cruise line names a ship after you? Princess Diana, evidently, wore this stunning red coat, along with a matching hat, when she boarded the "Royal Princess," a P&O cruise line ship named after her. On her right wrist, she's wearing a charm bracelet — a jewelry trend that has continued to recycle itself over the last few decades.

Diana, Princess of Wales wears a charm bracelet aboard the n
Diana wears a charm bracelet aboard the new P&O cruise liner "Royal Princess" named in honor of her.Tim Graham / Getty Images

The 'Revenge Dress,' London: 1994

Yes, this black off-the-shoulder dress with the sweetheart neckline looks unequivocally amazing on her — and for good reason. This dress is notoriously called "the revenge dress" due to the nature of the occasion: a dinner Princess Diana attended following the televised admission of adultery by her husband, Prince Charles.

Diana At Serpentine
Princess Diana arriving at the Serpentine Gallery, London, in a gown by Christina Stambolian, June 1994. Jayne Fincher / Getty Images

Cannes Film Festival: 1987

For the Cannes Film Festival in 1987, Princess Diana wore a baby blue gown, also designed by Catherine Walker, paired with a matching baby blue silk chiffon stole.

Diana Cannes Catherine Walker Dress
Princess Diana At The Cannes Film Festival, France. Tim Graham / Getty Images

London: 1988

Tennis aesthetics have skyrocketed in popularity in the last few years, from tennis skirts to shoes. Here, we see Princess Diana rocking her own sportswear, including a pair of classic, white leather Reeboks.

Princess Diana
Princess Diana at the Vanderbilt Racquet Club in London prior to a doubles match with David Verney, Steffi Graf and Club Secretary Charles Swallow.Gavin Kent / Getty Images

Italy: 1995

Oh, to be Princess Diana in Italy wearing a white Versace dress and kitten heels to match. We also love her clutch purse juxtaposed with her posh red nails.

Diana Versace Dress
Princess Of Wales Arriving At Concert In Italy To Raise Money For Bosnian Children.Tim Graham / Getty Images

Highgrove House: 1986

Diana frequented her country house in Highgrove with Prince Charles, although she reportedly compared being there with him to "prison." On this visit, she's wearing a pair of pink gingham pants (a pattern that's very trendy at the moment) and a hot pink matching sweater (or, jumper, as they might say in the U.K.)

Diana At Highgrove
Diana Sitting On The Steps Outside Her Country Home, Highgrove. The Princess Is Casually Dressed In Pink Gingham Trousers With A Matching Pink Jumper. Tim Graham / Getty Images

Guard's Polo Club: 1988

There are a few of Princess Diana's outfits that are in constant circulation on the internet, due in part to their unachievably casual vibe. This outfit is one of them. The Princess' crewneck paired with a blazer and ball cap already creates an impossible standard of casual chic — but by pairing it with straight-leg denim jeans and brown boots, she takes it to the next level.

Princess Diana Jeans Cowboy Boots
The Princess Is Casually Dressed In A Sweatshirt With The British Lung Foundation Logo On The Front, Jeans, Boots And A Baseball Cap.Tim Graham / Getty Images

London: 1995

Remember when we referenced the aforementioned Princess Diana unattainably casual outfits? This is one of the other ones.

This, perhaps, is one of Princess Diana's most legendary looks. Women across the globe continue to emulate this exact look, even going as far as to call the combination of bike shorts and an oversized sweatshirt the "Princess Diana gym look" when referencing it.

And, for some history behind the look: this photo was taken the morning before Princess Diana was set to give a televised interview (that was expected to be quite controversial) about Prince Charles and their marriage in November 1995.

Britain's Princess of Wales departs her London hea
Britain's Princess of Wales departs her London health club before her controversial TV interview later this evening. Johnny Eggitt / AFP via Getty Images

Buckingham Palace: 1981

Last, but most certainly not least: Princess Diana's romantic wedding dress, designed by David and Elizabeth Emmanuel. She also wears the Spencer family tiara as an homage to her roots.

Royal Wedding
The Prince and Princess of Wales on the balcony of Buckingham Palace on their wedding day in July 1981. Diana wears a wedding dress by David and Elizabeth Emmanuel and the Spencer family tiara. Terry Fincher / Getty Images


Royal Wedding
The Prince and Princess of Wales on the balcony of Buckingham Palace on their wedding day, 29th July 1981. Terry Fincher / Getty Images