Princess Diana's most influential outfit revealed - and it's not the revenge dress


Prince William and Prince Harry's late mother was one of the world's most prolific style icons, wearing many outfits people still copy today


Princess Diana in a red jacket with a bob© Getty Images
Laura Sutcliffe
Laura SutcliffeFashion and Beauty News Editor
1 hour ago
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It's almost 29 years since Princess Diana tragically passed away, but her memory lives on. When it comes to her elite fashion credentials, there was no one quite like King Charles' former wife.

She had an innate way of making every outfit she stepped out in look elegant, resplendent and trendy, and many of her looks are still prevalent today.

England's Princess Diana arriving in short light blue dress at the Royal Albert Hall for a performance of Swan Lake by the English National Ballet.    (Photo by Ken Goff/Getty Images)© Getty Images
Princess Diana was the ultimate style icon

It's hard to pinpoint her most influential outfit, as she wore so many standout ensembles during her life. But one that has stood the test of time is probably her most humble - cycling shorts with an oversized sweatshirt.

Princess Diana, Princess of Wales, wearing  Virgin Atlantic sweatshirt© WireImage
Diana made wearing cycling shorts very chic indeed

Many believe that the generic sporty separates are best suited to a gruelling workout, but over the past few years, cycling shorts have been adopted by many, from the Kardashians to Emily Ratajkowski, donning the super-tight separates as part of their glam wardrobe.

Diana, Princess of Wales, wearing a pale blue sweatshirt, pink cycling shorts and sunglasses, leaves Chelsea Harbour Club© Getty
Diana had many pairs of cycling shorts

Yet it is fair to say that Diana single-handedly made cycling shorts mainstream back in 1995.

Princess Diana after exercising at a gym in Earls Court, London in 1997
Princess Diana's now iconic look on the streets of London in 1997

The royal was snapped leaving the Chelsea Harbour Club, looking like the poster girl for glam gym attire. Teaming her pair of orange cycling shorts with a close-fitting, boxy sweatshirt, a black bag and trainers, she looked impossibly polished and fans at the time went wild for her dressed-down look.

Diana had numerous pairs of cycling shorts in a myriad of colours and wore them the same way each time - pairing them with an oversized separate on her top half, including her iconic 'Harvard' sweatshirt.

This look was ahead of its time, due to the sheer volume of people who still don this very ensemble almost 30 years later.

How Princess Diana's style is copied today

In 2024, Justin Bieber's beauty-mogul wife was pictured in Los Angeles, styling a pair of black cycling shorts with a large bomber jacket, a black T-shirt, socks and white trainers. Like Diana also sometimes did, she added a matching black Fila baseball cap and carried an immaculate Saint Laurent handbag. Diana, too, was known to carry a top-handled bag to the gym, often shunning a stereotypical, sporty carrier.

hailey bieber in sports shorts© GC Images
The beauty founder recreated Princess Diana's iconic post-gym moment

In 2025, Meghan Markle paid homage to her late mother-in-law, donning a Northwestern University sweatshirt, just like the one Diana wore in 1996. Prince Harry's wife attended Northwestern University in Evanston, Illinois, where she graduated with a double major in theatre and international studies in 2003.

Meghan Markle wearing a purple Northwestern sweater while smiling and walking through her garden© Instagram
Meghan wore a purple Northwestern sweater in 2025

Princess Diana, meanwhile, was photographed pairing the college sweatshirt with some cycling shorts and trainers while out and about in London.

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