1November 1995
Anwar Hussein//Getty ImagesThe 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."
2
WahdanID Princess Diana Fly Sweatshirt Vintage
An Etsy shop is selling a recreation of Diana's Virgin Atlantic sweatshirt, which she wore multiple times throughout her life. The actual sweatshirt was even auctioned off in 2019, of course, for a hefty price.
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Though a navy sweatshirt and creamsicle-colored biker shorts is not the most intuitive combination, the Princess of Wales illustrates that the two colors look even better together.
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Hanes Hanes 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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Diana's high top sneakers may appear all white, but they actually have a few black accents. These Adidas mid-rise sneakers are a similar style.
6August 1997
Tony Harris - PA Images//Getty ImagesThis is perhaps the most famous of the "Diana outfits." The Princess rewore her Harvard sweatshirt multiple times, usually paired with black spandex shorts and small circular glasses.
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7
Champion Champion Harvard University Crimson Classic Arch Crew-Neck Sweatshirt
Diana wore her sweatshirts baggy, often reaching mid-thigh. Make sure to size up for the same effortless look.
8
All Access Center Stage 6in Biker Short
The Bandier All Access 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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9
ray-ban OVAL @Collection
Ray-Ban offers a modernized version of Diana's oval glasses with silver frames. We love this green and black iteration.
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Colosseum Athletics 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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11
Lululemon lululemon Align Short 8"
When shopping for white spandex shorts, quality is key (you don't want any sheerness issues). Lululemon's Align shorts are sure to provide acceptable opacity.
12
Gucci Gucci Diana medium tote bag
Diana's purse was subsequently given her name. The Gucci Diana tote is a classic and will pair just as nicely with workwear as it does with athleisure.
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13October 1994
Mirrorpix//Getty ImagesThough 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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Old Navy Oversized Americana Sweatshirt for Women
Stars on top, stripes on the bottom, and cozy all over, Diana proved that flag-themed apparel is not just for July 4th.
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15
Alo Yoga High-Waist Biker Short - True Navy
Alo'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 New Balance NM1010
Like in her other ensembles, Diana paired this outfit with chunky white sneakers and white crew socks.
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17
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.
18April 1997
UK Press//Getty ImagesYet another USA item, Diana was not afraid to represent the nation across the pond.
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USA Oversized Crewneck Sweatshirt Cream
Princess Polly's crewneck sweatshirt is nearly identical to Diana's. Size up to truly get that Princess Di oversized feel.
20
Alo Yoga High-Waist Biker Short - Neon Pink
For some reason, though many of Diana's color combinations seem unusual, they always work. For example, she paired her red, white, and blue sweatshirt with fun, neon pink bike shorts.

Annie Goldsmith is the senior editor and digital lead at ELLE Decor, where she covers design, culture, style, and trends. She previously held positions at The Information, covering technology and culture, and Town & Country, writing about news, entertainment, and fashion. Her work has also appeared in Vogue, Rolling Stone, and the SF Standard.
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