Princess Diana's Best Fashion Moments of All Time

·9 min read
Princess Diana
Princess Diana

Anwar Hussein/WireImage / Jayne Fincher/Getty

Though Princess Diana's life was tragically cut short, her legacy continues to live on in many ways — one of which being her iconic style.

Part of what made her fashion so memorable was her ability to wear a glamorous ball gown one day and an oversized sweatshirt the next, with both looks being equally captivating. Throughout her time as Princess of Wales, Diana developed relationships with designers like Catherine Walker and Versace, but some of her most casual moments have sparked massive trends, such as the recent resurgence in athleisure. No matter what she wore, Princess Diana embodied a timeless elegance that will continue to have influence for decades to come.

Keep reading for a look back at some of Princess Diana's best fashion moments.

Princess Diana in London in November 1980

Lady Diana Spencer (later the Princess of Wales), who has been linked romantically with the Prince of Wales, being pursued by the Press near her London flat. Nineteen, she is the daughter of Earl Spencer
Lady Diana Spencer (later the Princess of Wales), who has been linked romantically with the Prince of Wales, being pursued by the Press near her London flat. Nineteen, she is the daughter of Earl Spencer

PA Images via Getty

Princess Diana, then Diana Spencer, was just 19 years old when she was first romantically linked to Prince Charles in 1980. That year, she was photographed dodging the paparazzi near her home in London, wearing a modest pinstripe skirt, red jacket and red handbag.

Princess Diana at Buckingham Palace in February 1981

Prince Charles And Lady Diana Spencer (later To Become Princess Diana) At Buckingham Palace On The Day Of Announcing Their Engagement
Prince Charles And Lady Diana Spencer (later To Become Princess Diana) At Buckingham Palace On The Day Of Announcing Their Engagement

Tim Graham Photo Library via Getty

The blue suit that Princess Diana wore for her engagement photos with Prince Charles was chosen in quite the roundabout way. The Royal Style in the Making fashion exhibition, which was presented in 2021 at the royal's former home of Kensington Palace, revealed that the then-19-year-old had first visited the Bellville Sassoon shop, but wasn't finding anything she liked. The sales associate, who didn't recognize her, suggested she try the nearby department store.

​​"You can imagine how Belinda [Bellville] and David [Sassoon] felt when they realized the future Princess of Wales had been turned away," curator Matthew Storey told PEOPLE. The Princess and her mother ended up returning to the Bellville Sassoon shop and selecting the blue suit, sparking a years-long collaboration between the brand and Princess Diana.

Princess Diana with Prince Charles in Scotland in May 1981

Prince Charles and Lady Diana Spencer hold a photocall with their dog Harvey at Craigowan Lodge in Balmoral, Scotland, 6th May 1981. This was their first official photocall after their engagement. Diana is wearing an Inca jumper with green corduroy trousers and Hunter boots
Prince Charles and Lady Diana Spencer hold a photocall with their dog Harvey at Craigowan Lodge in Balmoral, Scotland, 6th May 1981. This was their first official photocall after their engagement. Diana is wearing an Inca jumper with green corduroy trousers and Hunter boots

Tim Graham/Getty

For her first official photocall after their engagement, Princess Diana and Prince Charles posed alongside their dog Harvey at Craigowan Lodge in Balmoral, Scotland. The Princess wore a striped pink sweater with corduroy pants and Hunter boots.

Princess Diana at her wedding to Prince Charles in London in July 1981

Lady Diana Spencer (1961 - 1997) in her wedding dress designed by David and Elizabeth Emanuel
Lady Diana Spencer (1961 - 1997) in her wedding dress designed by David and Elizabeth Emanuel

Fox Photos/Getty

Princess Diana's famous wedding gown is a true testament to bridal fashion in the early 1980s. The ruffled collar, puffed sleeves and dramatic train are all notable elements of the ensemble, which was designed by Elizabeth and David Emanuel.

Princess Diana at the Victoria and Albert Museum in London in November 1981

Diana Princess of Wales at 'Splendours of the Gonzaga' exhibition at the Victoria and Albert Museum wearing a dress designed by Bellville Sassoon
Diana Princess of Wales at 'Splendours of the Gonzaga' exhibition at the Victoria and Albert Museum wearing a dress designed by Bellville Sassoon

Tim Graham Photo Library via Getty

Just four months after her royal wedding, the newly crowned princess was already looking the part. While visiting the Victoria & Albert Museum in November 1981, she wore a pale blue Bellville Sassoon gown and choker necklace.

Princess Diana at a fashion show in November 1982

The Princess of Wales arrives at the Guildhall in London for a fashion show, November 1982. She is wearing a blue dress by Bruce Oldfield. She is accompanied by her lady-in-waiting Anne Beckwith-Smith
The Princess of Wales arrives at the Guildhall in London for a fashion show, November 1982. She is wearing a blue dress by Bruce Oldfield. She is accompanied by her lady-in-waiting Anne Beckwith-Smith

Jayne Fincher/Princess Diana Archive/Getty

Princess Diana showed off a playful side of her fashion sense in this one-shoulder blue dress with ruffle details by Bruce Oldfield while at a fashion show at Guildhall in London.

Princess Diana in New Zealand in April 1983

Diana, Princess of Wales (1961 - 1997) visits the Pupuke School on the North Shore in New Zealand, April 1983. She is wearing a Catherine Walker suit and a John Boyd hat
Diana, Princess of Wales (1961 - 1997) visits the Pupuke School on the North Shore in New Zealand, April 1983. She is wearing a Catherine Walker suit and a John Boyd hat

Jayne Fincher/Princess Diana Archive/Getty

While visiting the Pupuke School on the North Shore in New Zealand, Princess Diana chose a more subdued look — a pale yellow Catherine Walker suit and a John Boyd hat.

Princess Diana at the London premiere of Back to the Future in January 1985

Diana (1961 - 1997), the Princess of Wales, attends the film premiere of 'Back To The Future'
Diana (1961 - 1997), the Princess of Wales, attends the film premiere of 'Back To The Future'

Keystone/Getty

Princess Diana's plum-colored velvet dress at the London premiere of Back to the Future may have looked simple from the front, but the dramatic low back makes it one of her most memorable looks. For even more drama, she added a long pearl necklace that draped down her back.

Princess Diana at the White House in November 1985

Diana Princess Of Wales, With Nancy Reagan At The White House, Wearing A Dress Designed By Fashion Designer Victor Edelstein
Diana Princess Of Wales, With Nancy Reagan At The White House, Wearing A Dress Designed By Fashion Designer Victor Edelstein

Tim Graham Photo Library via Getty

During a visit to the White House in Washington, D.C. (where she famously danced with John Travolta), Princess Diana wore a black, off-the-shoulder gown, black opera gloves and a pearl choker necklace.

Princess Diana at the National Gallery in November 1985

The Princess of Wales (1961 - 1997, later Diana, Princess of Wales) at a gala dinner at the National Gallery in Washington DC, 11th November 1985. She is wearing a white, crystal-beaded silk chiffon assymetric gown by Japanese designer Hachi
The Princess of Wales (1961 - 1997, later Diana, Princess of Wales) at a gala dinner at the National Gallery in Washington DC, 11th November 1985. She is wearing a white, crystal-beaded silk chiffon assymetric gown by Japanese designer Hachi

Tim Graham Photo Library via Getty

For a dinner at the National Gallery in Washington, D.C., the princess dazzled in a one-shoulder sequin gown by Hachi. She paired it with diamond earrings, metallic silver shoes and a clutch purse.

Princess Diana in Saudi Arabia in November 1986

Diana, Princess of Wales (1961 - 1997) arrives at Riyadh airport in Saudi Arabia, wearing a dress from Tatters, November 1986
Diana, Princess of Wales (1961 - 1997) arrives at Riyadh airport in Saudi Arabia, wearing a dress from Tatters, November 1986

Princess Diana Archive/Getty

For her visit to Saudi Arabia in 1986, Princess Diana wore a green-and-white dress by one of her favorite designers, Catherine Walker, along with white shoes, a white hat and a white clutch purse.

Princess Diana attending Easter mass in Windsor in April 1987

Diana, Princess Of Wales, With Her Son, Prince William And Her Nephew, Peter Phillips, On Their Way To Easter Service. The Princess Is Wearing A Pale Blue Coat Designed By Catherine Walker Who Made A Similar One For Prince William
Diana, Princess Of Wales, With Her Son, Prince William And Her Nephew, Peter Phillips, On Their Way To Easter Service. The Princess Is Wearing A Pale Blue Coat Designed By Catherine Walker Who Made A Similar One For Prince William

Tim Graham Photo Library via Getty

In celebration of the Easter holiday, Princess Diana wore a pastel blue coat by Catherine Walker as well as a matching hat and white gloves. Pictured here on her way to mass, she holds the hand of her son, Prince William, who is wearing a matching Catherine Walker coat.

Princess Diana at Cannes Film Festival in May 1987

Princess Diana At The Cannes Film Festival, France
Princess Diana At The Cannes Film Festival, France

Tim Graham Photo Library via Getty

Princess Diana arrived at the 1987 Cannes Film Festival dripping with glamour. She wore a strapless pale blue gown by Catherine Walker and a matching scarf as well as blue satin shoes.

Princess Diana at the Guards Polo Club in England in May 1988

Diana, Princess Of Wales At Guards Polo Club. The Princess Is Casually Dressed In A Sweatshirt With The British Lung Foundation Logo On The Front, Jeans, Boots And A Baseball Cap
Diana, Princess Of Wales At Guards Polo Club. 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 Photo Library via Getty

Princess Diana's 1998 appearance at the Guards Polo Club in Windsor is essentially a masterclass in looking casual yet chic. She took a simple sweatshirt and jeans and made it her own with cowboy boots, a blazer and a baseball cap.

Princess Diana in Dubai in March 1989

Diana, Princess of Wales, wears a Catherine Walker suit and a Philip Somerville turban hat during her official tour of the Gulf States on March 17, 1989 in Dubai, United Arab Emirates
Diana, Princess of Wales, wears a Catherine Walker suit and a Philip Somerville turban hat during her official tour of the Gulf States on March 17, 1989 in Dubai, United Arab Emirates

Georges De Keerle/Getty

While on her official tour of the Gulf States, Princess Diana visited Dubai wearing a blue-and-white suit by Catherine Walker and a turban-style hat by Philip Somerville.

Princess Diana at the British Fashion Awards in London in October 1989

Diana, Princess of Wales (1961 - 1997) at the first British Fashion Awards at the Royal Albert Hall in London, 17th October 1989. She is wearing a white gown by Catherine Walker with a waist-length jacket
Diana, Princess of Wales (1961 - 1997) at the first British Fashion Awards at the Royal Albert Hall in London, 17th October 1989. She is wearing a white gown by Catherine Walker with a waist-length jacket

Jayne Fincher/Princess Diana Archive/Getty

At the first British Fashion Awards at the Royal Albert Hall, Princess Diana showed off a slightly shorter hairstyle as well as a white gown and structured jacket by Catherine Walker.

Princess Diana in Budapest in May 1990

Diana, Princess of Wales, during her official visit to Hungary on May 8, 1990 in Budapest, Hungary
Diana, Princess of Wales, during her official visit to Hungary on May 8, 1990 in Budapest, Hungary

Georges De Keerle/Getty

In another matchy-matchy moment, Princess Diana wore a pink suit with purple trim during a trip to Hungary, which she accessorized with matching purple shoes and a purple clutch purse.

Princess Diana in Toronto in October 1991

Diana, Princess of Wales (1961 - 1997) arrives at Toronto airport for an official visit to Canada, 23rd October 1991. She is wearing a red, white and black Moschino suit and a hat by Philip Somerville
Diana, Princess of Wales (1961 - 1997) arrives at Toronto airport for an official visit to Canada, 23rd October 1991. She is wearing a red, white and black Moschino suit and a hat by Philip Somerville

Jayne Fincher/Princess Diana Archive/Getty

In the 1990s, Princess Diana began to branch out when it came to the designers she wore. On an official trip to Toronto, she wore a red-and-white houndstooth Moschino suit and Philip Somerville hat with black netting along the brim.

Princess Diana attending Easter mass in April 1992

Diana, Princess of Wales (1961 - 1997) with her son Prince William outside St George's Chapel, Windsor, at Easter, April 1992
Diana, Princess of Wales (1961 - 1997) with her son Prince William outside St George's Chapel, Windsor, at Easter, April 1992

Jayne Fincher/Princess Diana Archive/Getty

Hats are a major element of the royal wardrobe, and it seems like Princess Diana fully embraced the tradition. For Easter in 1992, she wore a black hat with yellow trim, complementing her yellow suit jacket and pleated skirt.

Princess Diana in Cairo in May 1992

Princess Diana (1961 - 1997) wearing a Catherine Walker suit with a hat by Philip Somerville on a visit to the Heliopolis War Cemetery in Cairo, 15th May 1992
Princess Diana (1961 - 1997) wearing a Catherine Walker suit with a hat by Philip Somerville on a visit to the Heliopolis War Cemetery in Cairo, 15th May 1992

Jayne Fincher/Princess Diana Archive/Getty

Princess Diana looked as demure as ever in a teal-and-white Catherine Walker suit and Philip Somerville hat while visiting the Heliopolis War Cemetery in Cairo.

Princess Diana arriving at the Serpentine Gallery in London in June 1994

Princess Diana (1961 - 1997) arriving at the Serpentine Gallery, London, in a gown by Christina Stambolian, June 1994
Princess Diana (1961 - 1997) arriving at the Serpentine Gallery, London, in a gown by Christina Stambolian, June 1994

Jayne Fincher/Getty

The very night that Prince Charles admitted on national television that he had been unfaithful to her, Princess Diana stepped out in what has gone down in history as the "revenge dress." While attending a gala at the Serpentine Gallery in London, photographers snapped now-iconic photos of the Princess wearing a fitted black off-the-shoulder dress with an asymmetrical hemline and chiffon train.

Princess Diana shopping in Knightsbridge in October 1994

Princess Diana shopping in Knightsbridge
Princess Diana shopping in Knightsbridge

Tom Wargacki/WireImage

Even when she was not making formal appearances, Princess Diana always looked elegant. While out shopping in London in 1994, she opted for a white mock neck top, fitted white pants and an olive green blazer. Her canvas and leather tote gave the look a laid-back feel.

Princess Diana at the Serpentine Gallery in London in June 1995

Diana, Princess of Wales (1961-1997), wearing a pale blue halter-neck dress by fashion designer Catherine Walker, as she attends a dinner hosted by Vanity Fair magazine at the Serpentine Gallery in Hyde Park, London, England, 27th June 1995
Diana, Princess of Wales (1961-1997), wearing a pale blue halter-neck dress by fashion designer Catherine Walker, as she attends a dinner hosted by Vanity Fair magazine at the Serpentine Gallery in Hyde Park, London, England, 27th June 1995

Princess Diana Archive/Hulton Archive/Getty

Showing this much skin was daring for a royal, but Princess Diana was a trailblazer through and through. In 1995, she wore a pale blue, knee-length Catherine Walker halter dress to a dinner hosted by Vanity Fair at London's Serpentine Gallery.

Princess Diana in Italy in September 1995

Princess Diana Attending A Concert In Italy In Aid Of Bosnian Children. The Princess Is Wearing A Short White Dress And White Shoes
Princess Diana Attending A Concert In Italy In Aid Of Bosnian Children. The Princess Is Wearing A Short White Dress And White Shoes

Tim Graham Photo Library via Getty

Leaning into her newfound fondness for midi dresses, Princess Diana wore a white Versace dress and matching white shoes while attending a charity concert in Italy.

Princess Diana in England in September 1995

Prince William arrives with Diana, Princess of Wales and Prince Harry for his first day at Eton College on September 6, 1995 in Windsor, England
Prince William arrives with Diana, Princess of Wales and Prince Harry for his first day at Eton College on September 6, 1995 in Windsor, England

Anwar Hussein/Getty

For Prince William's first day at Eton College in Windsor, Princess Diana wore a simple black dress, adding a pop of color with a double-breasted cerulean jacket.

Princess Diana leaving Chelsea Harbour Club in London in November 1995

Princess Diana, Princess of Wales, wearing Virgin Atlantic sweatshirt, leaves Chelsea Harbour Club, London in November, 1995
Princess Diana, Princess of Wales, wearing Virgin Atlantic sweatshirt, leaves Chelsea Harbour Club, London in November, 1995

Anwar Hussein/WireImage

Princess Diana's leisurewear continues to inspire fashion trends today, particularly this low-key combination of bike shorts, a sweatshirt and sneakers. Here, she wears a Virgin Atlantic sweatshirt while leaving the Chelsea Harbour Club in London.

Princess Diana in Argentina in November 1995

Princess Diana On Her Official Visit To Argentina
Princess Diana On Her Official Visit To Argentina

Tim Graham Photo Library via Getty

It was somewhat rare for Princess Diana to wear pink, but there's no denying that this bubblegum pink Versace suit, which she wore during an official visit to Argentina, was extremely flattering on her.

Princess Diana in Chicago in June 1996

Princess Of Wales In Chicago, USA, Arriving For Gala Dinner At Field Museum Of Natural History
Princess Of Wales In Chicago, USA, Arriving For Gala Dinner At Field Museum Of Natural History

Tim Graham Photo Library via Getty

Princess Diana tried purple on for size while attending a dinner at the Natural History Museum in Chicago. She paired this sleek, eggplant-colored Versace gown with matching shoes by Jimmy Choo and a choker necklace.

Princess Diana in Australia in October 1996

Diana, Princess of Wales at the Victor Chang Cardiac Research Institute dinner dance at the Sydney Entertainment Centre, Australia
Diana, Princess of Wales at the Victor Chang Cardiac Research Institute dinner dance at the Sydney Entertainment Centre, Australia

Tim Graham Photo Library via Getty

For a dinner dance in Sydney, Australia, Princess Diana wore a satin off-the-shoulder blue gown by Versace with a matching purse and shoes.

Princess Diana in London in 1997

Diana , Princess Of Wales, Opening The New Renal Unit At Great Ormond Street Hospital, London. The Visit Is Also To Celebrate The Variety Club's Gold Heart Day On Valentine's Day And The Hospital Also Celbrates It's 145th Anniversary. Diana's Suit Is By Fashion Designers Chanel.
Diana , Princess Of Wales, Opening The New Renal Unit At Great Ormond Street Hospital, London. The Visit Is Also To Celebrate The Variety Club's Gold Heart Day On Valentine's Day And The Hospital Also Celbrates It's 145th Anniversary. Diana's Suit Is By Fashion Designers Chanel.

Tim Graham Photo Library via Getty

This mint-colored Chanel suit was a refreshing choice for Princess Diana. She paired it with a simple nude pair of heels and a beige purse while attending an event in London.

Princess Diana in Bosnia in August 1997

Diana, Princess of Wales makes a three day visit to Bosnia - Herzegovina as part of her campaign to raise awareness about the devastating effects landmines have on peoples lives and to call for a complete ban on the production, sale and use of land mines. The trip was organised by the American-based Landmine Survivors Network. Here she is on the 2nd day of her visit. 9th August 1997
Diana, Princess of Wales makes a three day visit to Bosnia - Herzegovina as part of her campaign to raise awareness about the devastating effects landmines have on peoples lives and to call for a complete ban on the production, sale and use of land mines. The trip was organised by the American-based Landmine Survivors Network. Here she is on the 2nd day of her visit. 9th August 1997

Kent Gavin/Mirrorpix/Getty Princess Diana

During a three-day visit to Bosnia, Princess Diana proved, yet again, that some of her best fashion moments were the most simple. This pair of blue jeans with a crisp white button-down and brown leather belt is every bit as chic today as they were in 1997.

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