The Princess Diana Way To Wear Cycling Shorts

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Diana, Princess of Wales’ legacy extends far beyond her style. But there's no denying that the fascination with Lady Diana’s wardrobe is still going strong. From the Instagram account dedicated to “Lady Di’s sassiest post-divorce looks,” to the woollen Lanvin sheep sweater worn by Harry Styles, she still provides ample style inspiration 22 years after her untimely death.

During the '80s, the late royal's aesthetic was all vibrant colors and skirt suits, but Diana ticked off a number of key '90s trends in her time, too. Long before the Kardashian-Jenners, Bella Hadid, or the cast of Love Island tried out the cycling shorts trend, Princess Diana had already mastered it, all the way back in 1995. Her ability to turn an item usually worn for serious exercise into a certifiable trend outside the gym even inspired a Vogue Paris shoot featuring Hailey Bieber mimicking Diana's iconic cycling-shorts-and-university-sweatshirt look.

As the world gets used to our current reality and the UK goes into lockdown, it might be high time to change up your trusty trackies or leggings for a classic Lady Di-approved look perfect for working-from-home: the cycling short. So here's exactly how you can recreate Diana’s signature low-key athleisure look.

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The Color

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The famous Virgin Atlantic sweatshirt, given to her by brand founder Richard Branson, and then given from Diana to her trainer, Jenni Rivett, more than two decades ago was sold at the auction house RR Auction for $53,532 in July 2019. But arguably the real winner here was the highlighter orange cycling shorts she paired the jumper with.


Brighten up days inside with a vibrant-coloured offering from &Other Stories, available in sizes 32-44.


The Length

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Princess Diana liked her cycling shorts to peek out from beneath an oversized sweater, which means if you're looking to recreate her look, you'll need a mid-thigh length style.


This black pair from Sweaty Betty are the perfect Diana-style cut. Available in sizes XXS to L.


The Jumper

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Princess Diana's mix of color combinations kept the tried-and-tested formula fresh. This pink and blue combo will take you from WFH to home-workout.


A slogan sweatshirt speaks volumes when you're all Zoom-ed out. Available in sizes 6-14.


The Shoes

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Did Princess Diana also predict the return of the 'dad trainer'? It certainly seems so. Luckily it couldn't be easier to get your hands on a pair of chunky white trainers to complete the look.


Go full '90s with a chunky-soled trainer. Perfect for protecting the downstairs neighbours from impending at-home workouts. Available in sizes 4-7.