Princess Diana's Most Memorable Fashion Moments

(Image credit: Getty)

published 11 November 2020

From the moment Diana married Prince Charles in that famous bridal gown designed by David and Elizabeth Emanuel, her impeccable sense of style was recognized by the public. Throughout her marriage, and even more after her divorce, the princess became known for her bold sartorial choices and approachable accessibility. Even decades after her death, we're still looking to Diana for fashion inspiration, proving that she was truly timeless. In honor of the late-fashion icon, we're looking back at some of her greatest style moments.

1963

Honourable Diana Spencer, daughter of Viscount Althorp and his wife Frances, was born July 1, 1961, in Norfolk, England. A child of the aristocracy, Diana’s family had ties with the royals going back generations.

1963

Diana was the third daughter of the Spencers and her birth worried her parents about producing a male heir.

1967

Heartbreak was first introduced to Diana's life at a young age—she was just eight years old when her parents divorced.

1970

Diana spent most of her teenage years at school, where her generosity and big heart were recognized early on.

1974

Diana's grandfather died in 1975, so her father inherited the family title's, Earl Spencer, which resulted in Diana getting a title, Lady Diana.

1980

Diana's love for children started early on—in her pre-royal, "Sloane Ranger" days, she worked as a primary school assistant teacher and a nanny.

1980

Diana first wore her now-iconic black sheep sweater by Warm & Wonderful in 1980. She would wear it throughout her marriage to Prince Charles, which many took as a message about how she felt about her position within the royal family.

1981

Diana wore a blue suit for her official engagement announcement. Years later, when Prince William and Kate Middleton posed for their engagement portrait, the world drew similarities between Diana's suit from Harrods and Kate Middleton's Issa Phylis wrap dress.

1981

Here, in classic British garb (wellies!), an engaged Diana and Charles relax with their dog Harvey at Balmoral, the Queen's residence in Scotland.

1981

The public began to take note of Princess Diana's style when she wore a black strapless taffeta evening gown, designed by David and Elizabeth Emanuel, for her first public outing with her then-fiancé Prince Charles in March 1981.

1981

Lady Diana Spencer and Prince Charles's 1981 wedding was dubbed the "wedding of the century." Her dress, designed by David and Elizabeth Manuel, featured layers of taffeta, handmade lace, sequins, and 10,000 pearls.

1981

A few weeks after the frenzy of the royal wedding, Charles and Diana emerged in Scottish attire for a photo-op on the grounds of Balmoral Castle. The couple had just returned from their honeymoon cruise around the Mediterranean and these photos made Diana's plaid jacket and dress an instant hit.

1981

Princess Diana wore an off-the-shoulder lilac evening gown to an event in 1981, which became famous when she fell asleep in her seat wearing it. The palace was forced to announce her pregnancy to explain the faux pas.

1982

A newly married Diana dons a conservative coat dress designed by Arabella Pollen on a royal visit in Wales.

1982

A young, wide-eyed Diana sports a tartan coat at the Braemar Highland Games in Scotland.

1982

Princess Diana's maternity wear was well-received during her two pregnancies, but this green Belleville Sassoon maternity coat wasn't a stand-out piece until the Duchess of Sussex wore something very similar when pregnant with Archie Harrison.

1982

Less than a year after her marriage to Prince Charles, Diana gave birth to the much-anticipated royal heir, Prince William. Here, Diana and Charles stand on the steps of St. Mary's Hospital to introduce the little prince to the world. Her future daughter-in-law, Kate, also wore a polka dot dress debuting her and William's son, George, in 2013.

1982

New mom Diana rocks a ruffled blue dress by a favorite designer, Bruce Oldfield.

1983

Not only was the Victor Edelstein pink dress Diana wore during an early visit to Australia a smashing success with the press, her sapphire gems (given to her by the Crown Prince of Saudi Arabia) matched her blue engagement ring.

1983

It was in motherhood that Diana found a comfortable role in her royal life. Two years after giving birth to William, her youngest son Harry was born.

1983

Princess Diana and Prince Charles arrive in Perth, Australia for a royal tour. Diana was nicknamed the "People's Princess," because of her huge popularity with the public and in the press.

1984

When leaving the Lindo Wing after the birth of Prince Harry, Diana stepped out in a bright red coat dress, a red necktie, and ballet flats.

1985

While on a royal visit to Melbourne, Princess Diana attended a gala in a stunning one-shoulder aqua ballgown. But it was the emerald and diamond choker the Princess wore as a headband across her forehead that left a lasting impression.

1985

By far one of the most iconic dresses worn by Princess Diana was the black off-the-shoulder velvet evening gown she wore when she was twirled by actor John Travolta. The Princess wore the Victor Edelstein gown for a White House gala in 1985.

1986

Princess Diana, Prince William, and Prince Harry on one of their many vacations. She dressed William in a Dallas Cowboys t-shirt for the occasion.

1987

The light blue chiffon Catherine Walker evening gown Diana arrived in at the Cannes Film Festival had an elegance reminiscent of Grace Kelly.

1988

Navy and white stripes with a big white hat were Diana’s look of the day during a 1988 visit to Melbourne, Australia.

1988

A casual Diana always made headlines, and only further cemented her reputation as "The People's Princess." In 1988, she took a young Prince William to the polo grounds wearing high-waisted jeans, cowboy boots, a sweatshirt under a blazer, and a baseball cap.

1988

There has never, nor will there ever, be a greater mother-son twinning moment than Princess Diana and Prince Harry at the Trooping of the Colour in 1988. Diana wore an emerald green and white dress with a wide-brimmed hat, while Harry wore a white oxford shirt and overalls in the same color.

1989

Prince William and Prince Harry in their uniforms on the first day of school. The Princess opted for a monochromatic red look, which coordinated perfectly with the red details on her their uniforms.

1989

This diamond and pearl tiara, formally named the "Lovers Knot Tiara," was a wedding gift to the Princess of Wales from the Queen.

1991

Diana’s royal duties took her all over the world—this white and floral one-shoulder Catherine Walker dress was worn during a trip to Brazil.

1994

Princess Diana soon became a full-fledged fashion icon when she wore jaw-dropping dresses like this black off-the-shoulder number, which has since been dubbed her "revenge dress."

1996

Jewelry, like this layered pearl choker and her go-to big pearl earrings, were favorites of the late princess.

1996

In the late '90s, Princess Diana made news for making several trips to Pakistan. On her visit in 1996, she wore a light blue traditional Pakistani outfit, which caught a lot of attention in the press.

1996

A newly-divorced Diana wore this show-stopping blue dress to a dinner in Sydney, Australia.

1996

Princess Diana attended the Met Gala for the first time in 1996. The royal stunned in an iconic navy slip gown and satin duster designed by Dior's John Galliano.

1997

She traveled to Africa in the last years of her life to visit with those who had been wounded and injured by landmines, as well as advocate for the discontinued use of the practice.

1997

Here, she's seen with like-minded and like-hearted humanitarian, Mother Teresa.

1997

Just months before her death, Diana was photographed in an ice blue cocktail dress before catching a performance of Swan Lake at Royal Albert Hall in London. It was at this time that Diana was seeing Dodi Al-Fayed, with whom she died with in the car crash in Paris in August 1997.

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I'm an Associate Editor at the Business of Fashion, where I edit and write stories about the fashion and beauty industries. Previously, I was the brand editor at Adweek, where I was the lead editor for Adweek's brand and retail coverage. Before my switch to business journalism, I was a writer/reporter at PEOPLE.com, where I wrote news posts, galleries and articles for PEOPLE magazine's website. My work has been published on TheAtlantic.com, ELLE.com, MarieClaire.com, PEOPLE.com, GoodHousekeeping.com and in Every Day with Rachael Ray. It has been syndicated by Cosmopolitan.com, TIME.com, TravelandLeisure.com and GoodHousekeeping.com, among other publications. Previously, I've worked at VOGUE.com, ELLE.com, and MarieClaire.com.