How Princess Diana’s effortless shirt-and-shorts combo became our ultimate street style uniform

Written by Amy Beecham

She has (rightfully) been revered as one of the greatest style icons of all time, but some of her simplest looks have turned out to be the most enduring.

Today (31 August) may mark 25 years since Princess Diana was tragically killed in a car accident in Paris, but if you look around you’ll easily see her impact on the world hasn’t waned, from her humanitarian causes to fashion houses taking inspiration from her greatest looks.

As one of the most enduring style icons of the 20th century, the people’s princess will forever be synonymous with a uniform of preppy shirts, ankle grazing trousers, slogan jumpers and, of course, that revenge dress. But none of Diana’s outfits seem to have inspired the masses more than the humble sweatshirt-cycling shorts-chunky trainer combination.

Princess Diana favoured a pared-down uniform of slouchy sweatshirts over fitted cycling shorts

A staple of the princess’s paparazzi pics throughout the 90s, homages have been spotted everywhere, including high fashion runways, the LA streets on the likes of Hailey Bieber and on the bodies of fashion-forward Danes at the recent Copenhagen Fashion Week. The effortless, low-maintenance combination proves to be the go-to dressed down outfit du jour in 2022. Data reveals that  searches for ‘biker shorts’ have increased by 250%, ‘Princess Diana 80s’ by 90% and ‘Princess Diana 90s fashion’ by 100% worldwide.

Combining comfort and ease (you’ll likely find every element you need to emulate in your wardrobe already), it’s a perfect nod to the laid-back feel of the 90s without feeling too costume-like. 

How to replicate Princess Diana-inspired street style

Goose & Gander oversized sweatshirt

This colourful unisex style with a subtle logo is perfect for nailing the artfully oversized trend.

Shop Goose & Gander logo sweatshirt, £27.50

John Lewis graphic sweatshirt

Give a more overt nod to the 90s with this bold graphic jumper.

Shop John Lewis 1990 borg sweatshirt, £25

Adidas biker shorts (plus-size)

Coral doesn’t just have to be for summer. These comfy cotton shorts are available up to size 4X.

Shop Adidas biker shorts, £18.15

Girlfriend Collective biker shorts

Sustainably made and a zesty-lemon shade: what’s not to love?

Shop Girlfriend Collective high rise biker shorts, £40

Arket sporty cotton socks

These Arket socks are made with breathable cotton and are perfect for that varsity vibe.

Shop Arket sporty cotton socks, £15

H&M chunky trainers

If they look like your dad wore them during your childhood, we want them.

Shop H&M chunky trainers, £34.99

New Balance 57/40 trainers

Take a pop of colour from toe to top, instead.

Shop New Balance 57/40 trainers, £110

Images: Getty; courtesy of brands

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