November 1995
The Princess of Wales wore her Virgin Atlantic sweatshirt on multiple occasions. Diana’s trainer once noted that she kept re-wearing the crewneck to decrease the value of paparazzi shots. Jenni Rivett recalled, “I remember one of her strategies was that she was going to wear the same Virgin sweatshirt every single session.”
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Fly Atlantic Princess Diana Sweatshirt
An Etsy shop is selling a recreation of Diana’s Virgin Atlantic sweatshirt, which she wore several times throughout her life. The actual sweatshirt was even auctioned off in 2019 for a hefty price, of course.
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Old Navy High-Waisted Biker Shorts
Although a navy sweatshirt and orange biker shorts are not the most intuitive combination, the Princess of Wales illustrates that the two colors work even better together.
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Women’s 6-Pair Comfort Toe Seam Crew Socks
It’s not a Princess Diana spandex short outfit without a pair of white crew socks.
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Reebok x Anine Bing Freestyle Hi Shoes
Diana’s off-duty style was so iconic, it’s still inspiring designers today. When Anine Bing teamed up with Reebok to craft a new 2024 collection, her team instantly thought to f the princess. “Of course the images of Princess Diana walking the streets in her biker shorts and oversized crewnecks were on our creative mood board—I think the collection really embodies her off-duty ease and approach to style that is so timeless.”
See the full collection here.
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August 1997
This is perhaps the most famous of the casual “Diana outfits.” The Princess rewore her Harvard sweatshirt multiple times, usually paired with black spandex shorts and small circular glasses.
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New York Fashion Police Harvard University Sweatshirt
Diana wore her sweatshirts baggy, often reaching mid-thigh. Make sure to size up for the same effortless look.
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Alo Yoga High-Waist Biker Short – Black
The Alo Yoga biker shorts are beloved for a reason. You’ll certainly get a lot of wear out of this pair, whether you’re recreating a Diana look or simply slipping them on for exercising.
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Ray-Ban Oval Flat Lenses
Ray-Ban (a long-time royal family favorite brand) offers a modernized version of Diana’s oval glasses. We love this green and gold iteration.
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1996
Continuing her penchant for collegiate sweatshirts, Diana represented another American university, sporting a Northwestern sweatshirt and white shorts. Adding some luxury, Diana accessorized with a Gucci tote.
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Campus Colors Northwestern Wildcats Crew Neck Sweatshirt
A large, purple Northwestern sweatshirt is the key component of this look. Find a near identical version here.
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Lululemon Align High-Rise Short
When shopping for white spandex shorts, quality is key (you don’t want any sheerness issues). Lululemon’s Align shorts are sure to provide opacity.
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Gucci Diana medium tote bag
Named for the princess herself, the Gucci Diana tote is a classic and will pair just as nicely with workwear as it does with athleisure.
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October 1994
Though Diana was, of course, British, she seemed to enjoy the novelty of Americana-themed outfits, wearing American flag-adorned garments on multiple occasions.
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Anna-Kaci Casual American Flag Pullover Sweater
Diana proved that flag-themed apparel is not just for July 4th.
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Athleta Ultra High Rise Elation 7″ Short
Athleta’s biker shorts are often lauded for being both comfortable and flattering. A navy pair will complete your Diana-inspired look.
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New Balance Balance_550
Like in her other ensembles, Diana paired this outfit with chunky white sneakers and white crew socks.
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Cuyana Classic Structured Leather Tote
Though we’re not exactly sure what a princess needs to carry, Diana brought along the most versatile handbag option—a classic black tote. (We love this version from editor- and Meghan Markle-favorite brand Cuyana)
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April 1997
Yet another USA item, Diana was not afraid to represent the nation across the pond.
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Dressmine USA Long Sleeve Sweatshirt
This crewneck sweatshirt is almost identical to Diana’s. Size up to truly get that Princess Di oversized feel.
Annie Goldsmith is the news writer for Town & Country, where she covers culture, politics, style, and the British royal family.
Lauren Hubbard is a freelance writer and Town & Country contributor who covers beauty, shopping, entertainment, travel, home decor, wine, and cocktails.
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