Princess Diana’s Best Fashion Moments of All Time

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

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

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

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

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

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

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

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

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

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

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

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

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 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

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

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

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

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

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

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 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

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

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

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

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

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’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

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 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

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

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

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.