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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

Diana, Princess of Wales (1961 - 1997) wearing 'Black sheep' wool jumper by Warm and Wonderful (Muir & Osborne) to Windsor Polo, June 1981
Princess Diana casual looks: The famous black sheep sweater in 1981Getty

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.

2. Pre-wedding wellies

Princess Diana and Prince Charles in 1981
Princess Diana and Prince Charles in 1981Getty

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

Princess Diana wearing a koala sweater while pregnant in 1982
Princess Diana in 1982Getty

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!

4. A terrific tracksuit

Princess Diana in a tracksuit in 1985
Princess Diana in 1985Getty

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, Princess of Wales (1961 - 1997) sitting on a step at her home, Highgrove House, in Doughton, Gloucestershire, 18th July 1986
Princess Diana in 1986Getty

Diana’s matching checkered capris and pink sweater were charmingly girly without being fussy.

6. Summer overalls

Princess Diana in overalls in 1986
Princess Diana in 1986Getty

Who says overalls are just for kids? Certainly not Princess Diana, seen here in a summery white pair.

7. Charitable and comfy

Princess Diana in casual outfit in 1988
Princess Diana in 1988Getty

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

Princess Diana in 1989
Princess Diana in 1989Getty

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

The princess with William and Harry in 1993
Princess Diana with William and Harry in 1993Getty

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

The princess wearing a pale blue sweatshirt, pink cycling shorts and sunglasses, leaves Chelsea Harbour Club on August 24, 1994 in London, United Kingdom
Princess Diana casual looks: Bike shorts in 1994Getty

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

The princess wearing Virgin Atlantic sweatshirt, leaves Chelsea Harbour Club, London in November, 1995
Princess Diana in 1995Getty

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

The princess in khakis in 1997
Princess Diana in 1997Getty

In 1997, the year of her untimely death, Princess Diana wore khakis, a white button-down and loafers — a timeless casual yet polished look.

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