12 Casual Looks That Prove Princess Diana Was Always a Style Icon
The People's Princess made bike shorts look just as fabulous as couture
Princess Diana was known for her grace, empathy and style, and over 25 years after her tragic death, she still captivates women of all ages, and her impact on fashion can still be deeply felt. While the tall, blonde, blue-eyed royal looked stunning in ’80s and ’90s couture, her more casual looks have become surprising staples of social media feeds in recent years.
As one of the most closely scrutinized and photographed women in the world, Diana wasn’t just documented wearing expensive gowns. She was also often seen in casual outfits including sweatshirts and bike shorts. These outfits captured the approachable nature that led her to be known as “the People’s Princess,” and years later they’ve stood out as some of her most enduring looks of all.
Here’s a look at 12 of our favorite Princess Diana casual looks that prove comfort and chic go hand in hand.
1. The black sheep of the royal family
In the early ’80s, the young princess was frequently seen wearing this adorable knit sweater covered with sheep. The sweater, which came from the knitwear line Warm & Wonderful, had a symbolic resonance for Diana, as it featured a lone black sheep on the front, which served as a tongue-in-cheek commentary on her status as an outsider in the royal family.
The much-discussed sweater sold for a jaw-dropping $1.14 million at a 2023 auction, and has been reissued in recent years, so even non-royals can buy it.
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2. Pre-wedding wellies
Shortly before her wedding to Prince Charles, Diana wore a colorful patterned sweater with baggy pants and high rubber rain boots. The boots, made by the brand Hunter and known as Wellingtons, or wellies for short, have long been a staple of the casual British wardrobe.
3. Koala cuteness
Diana loved a novelty knit as much as the next ’80s girl, and while pregnant with Prince William, she wore this whimsical koala sweater by Australian designer Jenny Kee — the perfect casual look for a mama-to-be!
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4. A terrific tracksuit
Tracksuits aren’t what you’d usually consider part of the royal wardrobe, but when the princess wore a black and yellow one it didn’t look the least bit frumpy.
5. Pretty in pink
Diana’s matching checkered capris and pink sweater were charmingly girly without being fussy.
6. Summer overalls
Who says overalls are just for kids? Certainly not Princess Diana, seen here in a summery white pair.
7. Charitable and comfy
Diana was known for her dedication to charitable causes, and in this shot, she wore a sweatshirt promoting the British Lung Foundation. The blazer on top gave the casual look a touch of polished tailoring, while a baseball cap and boots added offbeat charm.
The foundation, now known as Asthma + Lung UK, sells a reissued version of the sweatshirt, for those wishing to channel Diana’s style — and her desire to help others.
8. Outfit repetition
While Diana had an unlimited, expensive wardrobe at her disposal, she was often seen wearing the same clothes and accessories more than once. In this picture of Diana after dropping William and Harry off at school, she wore the same baseball cap and boots as in the previous photo. The billowy pants tucked into the boots are a particularly unexpected touch.
9. Double denim
Double denim is usually considered a fashion don’t, but in this ski trip snapshot, Diana, seen with little William and Harry, made a denim-centric outfit look downright sophisticated.
10. Royal bike shorts
No one rocked a pair of bike shorts quite like Diana, and she was often seen wearing a sweatshirt over a pair of these shorts during trips to the gym. The casual cool of the pink bike shorts, blue sweatshirt and white sneakers (or as the Brits would say, trainers) still feels fresh today.
11. Come fly with me
In this off-duty shot, Princess Di paired a Virgin Airlines sweatshirt with peach bike shorts and chunky white socks and sneakers, making for a very ’90s silhouette.
Diana wore the Virgin sweatshirt, which was given to her by the brand’s founder, Richard Branson, frequently and reportedly hoped that by rewearing it, she wouldn’t be photographed as often, and could be left alone (alas, this wasn’t the case). The sweatshirt sold for $53,532 at an auction in 2019.
12. Classic khakis
In 1997, the year of her untimely death, Princess Diana wore khakis, a white button-down and loafers — a timeless casual yet polished look.
