Where protocol and image were prioritized within the British royal family, Princess Diana focused on creating a genuine connection with people from the start. Whether serving as a patron to artistic organizations like the English National Ballet, helping to end the stigma around HIV/AIDS by removing her gloves to shake hands with a patient, or participating in a barefoot race with other parents at her son’s school, Diana brought a refreshing approachability to the royal family. It was this break from rigidity and formality, in fact, that helped to cement the Princess of Wales as the “people’s princess.”

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In many ways, that authenticity was reflected in Princess Diana’s wardrobe, too. Just 20 years old when she married Prince Charles (now King Charles III) in a televised ceremony viewed by more than 750 million people around the world, Diana’s earliest looks mirrored the frills and the ruffles of the early ‘80s. But even then, there were glimmers of her personality in her royal wardrobe. The Princess of Wales would often repeat gowns from royal engagements to red carpet events (and vice versa), and she found inventive ways to accessorize with her jewelry—from wearing an emerald necklace as a headband to redesigning a sapphire brooch into her most memorable pearl choker.

She also took into consideration the cultures of the countries she was visiting during official royal tours to places like Japan and Pakistan. “My wife and I spent a great deal of time researching what she wore for official visits abroad, even visiting countries in advance to make sure we had it right,”recalled Said Cyrus, the husband of Diana’s go-to designer Catherine Walker. “We tried to ensure that our designs bridged her ambassadorial role for her own country and also paid respect to each destination.”

Following her separation from Prince Charles in 1992 (the pair finalized their divorce in 1996), Princess Diana’s style shifted to reflect her newfound independence. Bright colors were still a part of her wardrobe, but she also added more neutrals, most often turning to Gianni Versace for tailored suits and sleek evening gowns. Her handbag of choice also became a focal point, with several fashion houses later renaming popular bags in her honor. There was the Gucci tote with bamboo top handle, that would officially be renamed the Gucci Diana when then-creative director Alessandro Michele reissued the bag in 2021, and Tod’s renamed one of its leather totes the Di bag as well. Most famous of all was the Dior Chouchou bag, which was first gifted to Diana by France’s first lady Bernadette Chirac in 1995, and became such a constant accessory for the Princess of Wales that within a year, the French fashion house changed its name to the Lady Dior.

And then, there was her off-duty style. While polo matches and school runs often meant pairing denim with blazers and flats, it’s Princess Diana’s workout wear, which combined oversized sweatshirts, bicycle shorts, crew socks and sneakers, that continues to be emulated today. Ahead, revisit some of Princess Diana’s best fashion moments—from royal tours in custom evening gowns and diamond tiaras to off-duty athleisure looks.

To officially announce their engagement, a 19-year-old Lady Diana Spencer wore a blue skirt suit that matched her sapphire and diamond engagement ring as she posed alongside Prince Charles in the gardens of Buckingham Palace. Before she suddenly found herself in the spotlight, she had been working as a teacher’s assistant at a nursery school in London.

One of the earliest examples of Diana’s off-duty style, the princess-to-be attended a polo match just weeks before her wedding in buttercup-yellow overalls that she wore with a floral print blouse, espadrille sandals and sunglasses.

In a ceremony more extravagant than any fairytale, Lady Diana Spencer became the Princess of Wales when she wed Prince Charles at St. Paul’s Cathedral in London. For her walk down the aisle, which would make history as the first televised royal wedding, Diana wore a silk-taffeta design by David and Elizabeth Emanuel. The very ‘80s gown included oversized sleeves and a full skirt, with nearly 10,000 mother of pearl sequins hand-sewn along the bodice and sleeves (and the 40-foot-long veil). An impressive 25-foot detachable train trailed behind the princess, who also wore custom slippers by Clive Shilton, the Spencer family diamond tiara and diamond drop earrings.

To attend an exhibition at the Victoria & Albert Museum, Diana wore a shimmering pastel gown by Bellville Sassoon that was........

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