Why Princess Diana’s Timeless Off-Duty Style Is Still Being Recreated Around the World

Princess Diana’s style in one word? Timeless.

PRINCESS DIANA AND PRINCE HARRY LEAVING HARBOUR CLUB GYM, PRINCESS DIANA 1ST DATE SINCE DIVORCE WITH CHRIS WHALLEY, and Britain's Princess of Wales departs her London health club

She passed away before I was even born, but even now, nearly three decades later, I’m taking tips from the Princess. More specifically, my Roman Empire is her off-duty style, like all the times she wore shorts, sweatshirts, and sneakers — which was actually pretty often. And celebrities like Hailey Bieber and Cardi B are still making references to it.

Each sighting was slightly different from the last, but fundamentally the same. They consisted of crewnecks (her iconic Virgin Atlantic pick eventually sold for $50,000 at an auction) and varying biker shorts.

Princess Diana’s Outfit Blueprint

  • Sweatshirts: Barnesmith Crewneck Sweatshirt, $45
  • Efan Oversized Sweatshirt, $20 with coupon (orig. $28)
  • Orandesigne Oversized Graphic Sweatshirt, $28
  • Anrabess Oversized Crewneck Sweatshirt, $25 (orig. $36)
  • Biker Shorts: Baleaf 8-Inch Biker Shorts, $20 (orig. $27)
  • Leggings Depot Biker Shorts, $14
  • Tote Bags: Bagsmart Tote Bag, $32
  • Cocifer Top-Handle Tote Bag, $28 with coupon (orig. $30)
  • Dasein Top-Handle Bag, $39 with coupon (orig. $43)
  • Sneakers: Illude Chunky Platform Sneakers, $27 (orig. $30)
  • Reebok Classic Harman Run Sneakers, $36 (orig. $65)

Barnesmith Crewneck Sweatshirt

Amazon

Since Northwestern is my alma mater (and Meghan Markle’s), I’m obviously going to take the most literal approach to recreating Diana’s outfit. But for someone else, it’d be just as simple as choosing a sweatshirt for your school, team, or city, like this Los Angeles sweatshirt.

And remember: Style is personal, so it’s A-okay to make a few tweaks here and there. One that I might implement on a day when I’m not in the mood to rep anything? Wearing a plain hoodie or crewneck like this one. Plus it’s “super soft and fuzzy” on the inside, according to one shopper.

Baleaf 8-Inch Biker Shorts

Amazon

I don’t like leggings, but biker shorts are much more freeing. And I practically live in them during transitional seasons when the weather hits that sweet spot between hot and cold. Diana donned multiple colors, and I plan to do the same, although probably not in white since I fear they may be see-through.

These ones from Baleaf come in three lengths, so as someone who’s fairly tall, I can wear them with confidence. They’ve also racked up thousands of perfect ratings. But if it’s coral I’m craving, I’d step out in this $14 pair that looks like Diana’s and also feels “like butter.”

Cocifer Top-Handle Tote Bag, $28 with coupon

Amazon

Diana’s totes ranged from styles with top handles — a detail her daughter-in-law Kate Middleton is fond of — to those with longer handles that she could wear hands-free. While this highly praised purse is the former, it also has a crossbody strap, so it can be worn either way.

Illude Chunky Platform Sneakers

Amazon

And since it wouldn’t make sense to wear a comfy, casual outfit with a pair of sandals or flats, I’m due for another pair of sneakers. I’ve always been tough on shoes, so I don’t always like to shell out a ton of cash on them. These are only $27, though, and have a padded insole, so they should be at least semi-comfortable.

Keep scrolling to shop more sweatshirts, biker shorts, sneakers, and tote bags inspired by Princess Diana now.

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