When Princess Diana was first introduced to the public as Prince Charles’ (now King Charles III) future bride in 1981, she became an instant global attraction, with news articles being written about every aspect of her life—especially her style.

Diana became the pin-up princess of the 1980s and 1990s, with her expansive wardrobes boasting hundreds of ballgowns, evening dresses and suits for every occasion.

The princess graced the cover of British Vogue, attended the Met Gala and was friends with some of the biggest names in fashion, many of whom dedicated designs and collections to her.

Despite the initial fairytale image projected onto Diana in the early 1980s, by the 1990s the public were increasingly aware of the negative aspects of her life, such as troubles in her marriage that led to formal separation in 1992 and divorce in 1996, to struggles with her mental health and the media.

However, throughout the 1990s the princess began to take control of her life and her image, outwardly displaying a newfound confidence and independence through her style and fashion.

At the time of her tragic death following a high-speed Paris car crash in 1997, Diana was regarded as one of the most fashionable women in the world.

In the over two decades since her death, the princess’ 90s looks are still replicated and referenced by designers and celebrities from the catwalk to sidewalk around the world.

Here, Newsweek looks at ten of Princess Diana’s most glamorous 1990s fashion moments, from movie premieres to charity galas and her poignant final public engagement.

Graphic Christening

In December 1990, Princess Diana made her aesthetic transition from the excesses of the 1980s to the streamlined chic of the 1990s clear with the outfit she chose to wear for the christening of her niece, Princess Eugenie.

At Queen Elizabeth II’s Sandringham home in Norfolk, England, the princess made a striking impression in a monochrome houndstooth skirt-suit from Italian fashion brand Moschino.

Red Carpet Ready

Never shy of a dramatic red carpet moment, Diana made many appearances at movie and theater premieres during the course of her public life.

In September 1991 she attended the gala showing of Stepping Out starring Liza Minelli, wearing a one-shouldered asymmetric gown designed by one of her favorite fashion designers, Catherine Walker.

The dress featured cherry blossom motifs created with pale pink sequins and was also worn for an official visit to Brazil in April the same year.

The Revenge Dress

Perhaps the most famous dress that Diana ever wore was debuted in June 1994 for a charity event at a London art gallery on the evening Prince Charles gave a television interview admitting he had been unfaithful to his wife.

For the event, Diana chose a daringly low-cut, short-skirted black cocktail dress designed by Christina Stambolian and was unlike anything she’d worn in public before.

The dress ensured her photographs made the front pages of the newspapers the next day, alongside coverage of Charles’ interview, with the press thus giving it the nickname the “Revenge Dress.”

Fashion Friends

One of Diana’s closest friends in the fashion world was designer Gianni Versace.

In 1995, Versace designed an entire collection around Diana, naming it “Conservative Chic.” The looks included a number of simple shift dresses and classically tailored skirt suits.

Diana wore a large number of pieces from the collection, including a pink suit for which she and the designer referenced former first lady Jacqueline Kennedy.

Diana wore the suit for an official visit to Argentina in November 1995.

Gianni Versace and Diana died within weeks of one another in 1997, with Diana’s fatal car crash following the fashion designer’s murder outside his Miami home.

Sydney Gala

One of Versace’s most memorable creations for Diana came in the form of a sleek cobalt blue evening gown with asymmetric neckline.

The dress was worn once publicly by the princess, at a charity gala given during an official visit to Sydney in October 1996, soon after her divorce from Prince Charles was finalized.

Met Gala

One of the fashion world’s most prestigious annual events is the Costume Institute’s fundraising gala at the Metropolitan Museum of Art, nicknamed the “Met Gala.”

Diana attended the event only once, at the invitation of her friend, Harper’s Bazaar editor Liz Tilberis. The evening marked the opening of an exhibition dedicated to the life and career of French fashion designer Christian Dior.

For the event, Diana commissioned a gown from the debut collection of Dior’s new head creative director, John Galliano, and she made a striking impression in a bias-cut silk slip dress inspired by a lace-embellished nightgown.

Charity Awards

As Diana moved into the mid-1990s, she adopted a new uniform of simple skirt suits and shift dresses for official occasions, in an effort to draw more attention to her charitable causes and not her style choices.

A core example of this style was worn to a charity awards ceremony at the Savoy Hotel in March 1997. For the event the princess chose a pale pink suit with rolled cuff and collar details and mother-of-pearl buttons designed by Catherine Walker.

Swan Lake

Diana was a dedicated lover of ballet and in June 1997 attended a performance of Swan Lake at the Royal Albert Hall in London.

On the evening, the princess wore a chic mini dress embellished with crystals by one of her favorite designers at the end of her life, Jacques Azagury.

The hemlines of the princess’ skirts became shorter after her divorce and combined with the square-cut neckline showed her developed suntan to its best advantage.

Simply Red

One of the princess’ final overseas visits was made to Washington D.C. in June 1997 to attend events connected with her personal ambition to end the use and manufacture of anti-personnel landmines around the world.

During the trip, Diana attended an American Red Cross gala and in tribute she wore a vivid red evening gown with a trailing waist tie addition accentuating her height, designed by Jacques Azagury.

Final Engagement

Red was also the color of the very last dress that Diana wore for a public engagement before her untimely death at the age of 36 in August 1997.

Weeks before, the princess laid a foundation stone at a hospital in England, wearing a classic red shift dress with double gold buckled belt designed by Catherine Walker.

The dress has been replicated in the upcoming sixth and final season of Netflix’s The Crown.

James Crawford-Smith is Newsweek‘s royal reporter, based in London. You can find him on X (formerly Twitter) at @jrcrawfordsmith and read his stories on Newsweek‘s The Royals Facebook page.

Do you have a question about King Charles III, William and Kate, Meghan and Harry, or their family that you would like our experienced royal correspondents to answer? Email [email protected]. We’d love to hear from you.