princess diana walking in a parking lot

Most of the world may remember Princess Diana as a humanitarian glowing in a tiara, but if you check out her casual style—the moments between gym visits and black-tie galas—she was ahead of her time. As a figure whose star rose in tandem with the emerging paparazzi machine, Princess Diana knew there was no such thing as “off duty.” She was always on. And the fashion playbook she wrote in the ’80s and ’90s makes perfect sense now, in a moment when Whole Foods checkout-line looks are as thought-out as Fashion Week fits. It’s no mystery why candid images of her flood the nostalgia torrent of Instagram—or why Virgil Abloh recently dedicated an entire Off-White show to her.

princess diana sits in the passenger seat of a car
She wore this sweater—with a black sheep on its front—in the midst of her friction with the royal family.

Bob Thomas / Popperfoto / Getty Images

Her best looks read like a mood board of the past five years in fashion: The Harvard sweatshirt paired with white spandex shorts and an Hermès bag. Her treasured Philadelphia Eagles varsity jacket thrown over trousers or a pencil skirt. The Sony baseball cap, plastic goggles, and pearl choker donned during a factory tour. Yowza! And yes, Frank Ocean posted it on his Instagram. The outfits are so precise, so cool, and occasionally so bizarre that they tell us more about her—her sense of daring and her egalitarian approach to getting dressed—than any official royal portrait could.

princess diana walking in gym clothes
Before there was athleisure, there were just gym clothes. Diana’s approach: precise, cool, bizarre.

Anwar Hussein / Wireimage / Getty Images

princess diana walking wearing a red coat and leather bag
Even a trip to the gym demands your best outerwear and finest leather goods.

Reuters Images

princess diana wearing a pink sweater jeans pink chuck taylors sunglasses and a bandana
Everything here is a basic—Chuck Taylors, handkerchief, carpenter jeans, crew neck sweatshirt, aviators—but together, they have bizarre panache.

Glenn Harvey/Camera Press/Redux

princess diana walking around the back of a car in a harvard sweatshirt
Forget going to Harvard. Wearing bike shorts and a Harvard sweatshirt with the sleeves perfectly bunched is just the right kind of elitist mystique.

Kieran Doherty/Reuters

There’s a kookiness to her personal style that defined her own vision of luxe, almost a series of running jokes about “fanciness.” She became obsessed with a blue mesh baseball cap sporting the comically imposing crest of the Royal Canadian Mounted Police. That, along with her Northwestern and Harvard sweatshirts, feels like some eccentric tussle with status and regality. Isn’t it fun to think that a woman who had to wear a crown also wore a baseball cap embroidered with one? Especially when she paired it with sweatpants that she tucked into cowboy boots—and then threw on a blazer to complete the ensemble. Three decades later, it still looks so right that you want to compose an entire treatise titled “Consider the Sweat Suit.”

princess diana leaves a building
Menswear was soundly in her repertoire, but she did it her way, with lots of gold Escada elephants.

Julian Parker / UK Press / Getty Images

All those casual classics in her wardrobe are designed for comfort, but Diana worked them with the same intention that she put into a Versace gown. You can observe the way she saw value in everything: A sweatshirt can be as interesting as precious knitwear. Something with a drawstring can be tuxedo-level sharp. If democracy is inherent to luxury—anyone can feel it, and any garment can be it—Diana was the royal who led us there.


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