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.
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.
© WireImageMany 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.
© GettyYet it is fair to say that Diana single-handedly made cycling shorts mainstream back in 1995.
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.
© GC ImagesIn 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.
© InstagramPrincess Diana, meanwhile, was photographed pairing the college sweatshirt with some cycling shorts and trainers while out and about in London.
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