Image via @haileybieber

When we think of style icons, it’s easy to allow your mind to go straight to Kim Kardashian or Rihanna, but when we look back at the real streetwear legends of year’s past, it’s impossible not to think of the late, great Diana Spencer – Princess of Wales. With the iconic “revenge dress” at the forefront of everyone’s memory, it’s easy to forget that Princess Di had a penchant for bike shorts, varsity sweatshirts and fresh kicks, but here at The Sole Womens, we can’t get over Diana’s perfectly imperfect ‘90s look, and Instagram agrees.

In a recent photoshoot for Vogue Paris, Hailey Bieber (a cool-girl style hero in her own right) expressed her love for Diana’s athleisurewear looks and reinterpreted some of Di’s most well-known ensembles. Opting for Lycra bike shorts and baggy jumpers, Bieber nailed the look with sporty ankle socks and a pair of white sneaks. In one of the images, Bieber even holds her car keys in her mouth which is a direct nod to a snap of Diana leaving the gym back in the ‘90s. Posting on her Instagram, Hailey Bieber wrote: “ all credit and inspo to the amazingly beautiful and iconically stylish Princess Diana who I’ve looked to for style inspiration for as long as I can remember. Thank you for leaving behind such an iconic fashion and style legacy.”

Hailey Bieber isn’t the only millennial fan of Princess Di. It’s virtually impossible to find a celeb that hasn’t looked to her for inspiration at some point in their style career; the Hadid’s love to rock a bike short and baggy tee combo, Kendall Jenner has a penchant for light-wash denim and oversized blazers and there are several red-carpet moments from Rihanna, Dakota Fanning and Zoë Kravitz that nod to styles brought to the forefront by Diana. Even fashion-dragon Anna Wintour held the princess in high regard, saying: “Whether it was attending a charity event or wearing a designer, she did a world of good.”

However, it wasn’t all ball gowns and bike shorts for Diana; her wardrobe was vast and unapologetic. Back in 1981, Di paired a floral shirt with pastel yellow dungarees and pink espadrilles and, quite frankly, the entire outfit belongs in our 2020 summer capsule. Never one to shy away from a splash of colour, Diana practically lived in varying shades of yellow, red or blue and in 1987 she made headlines when she donned one of her most iconic gowns at the Cannes Film Festival – the baby-blue dress by Catherine Walker. This gown has been recreated time and time again and in 2019, Priyanka Chopra made her Cannes Debut in an updated version of the iconic dress.

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Gowns, galas and Princess-esque polish aside, Diana paved the way for modern street style. She rocked some of her best looks when heading to and from the gym but somehow always managed to maintain an unflappable air of elegance. In winter, she would chuck her favourite tailored maxi coat over her kit and her chunky sneakers would peep out from the bottom offering a serious hit of relatability. Looking to baggy jeans and fresh Converse Chuck 70s on off-duty days, oversized sunglasses were a must for Di and teaming crisp tailoring with athleisurewear basics was an everyday occurrence.


When it came to footwear, Diana was no stranger to a crisp white pair of Superga sneakers which her daughter-in-law, Kate Middleton, is also partial to. But when it came to the gym, Diana was often spotted in her favourite pair of Reebok sneaks. Paving the way for sneakerheads of the future, her iconic tube-sock-and-chunky-sneaker combo is one of the simplest, most accessible trends of all time and remains a staple for women across the globe.

Proof that a real-life princess can be relatable, accessible and just like us, Diana’s fearless wardrobe was unprecedented during her time with the Royal Family. Inspiring people across the globe to spice up their casual wardrobe with a few key accessories – like a clean leather handbag or some chic sunnies – Diana gave birth to the athleisurewear trend way before the world was ready to see it. Now, with bike shorts and your favourite comfy sweatshirt counted as your most treasured everyday pieces, it’s easy to forget that the comfy-casual trend was around way before the Kardashians.

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Forever a style icon 🙌🏼 (📷: Getty)

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If you want to dress like Diana, we’ve rounded up our favourite oversized sweatshirts, bike shorts and chunky trainers and included them below.

Nike Oversized Jumper | Buy now at ASOS

Atlanta Sweatshirt | Buy now at ASOS

Puma Bike Shorts | Buy now at ASOS

Nike Bike Shorts | Buy now at ASOS

adidas Originals Ozweego Trainers | Buy now at ASOS

Superga Trainers | Buy now at ASOS