It's Finally Princess Diana Outfit Season
Because we all know that Princess Di was the queen of transitional style.
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It's here. Those few weeks between summer and fall where you throw on your favorite crew neck sweatshirt, a pair of spandex biker shorts, and ask yourself (as has become a TikTok trend), "Am I... Princess Diana?" It feels like about two seconds when the beloved Princess of Wales's favorite outfit makes sense—not hot enough to be sweltering in a sweatshirt, but not so freezing to preclude bare legs. September is prime Princess Diana outfit time.
Lady Di wore the look on many occasions, often while heading to or from the gym. The combination is simple: sweatshirt, biker shorts, crew socks, and chunky white sneakers (plus, often, her car keys). In the past year or so, there's been a resurgence in the style, as spandex shorts have come back into fashion, thanks to celebrities like Bella Hadid and Hailey Bieber. At the same time, sneakers have gotten chunkier, sweatshirts have gotten larger, crew socks replace the no-shows, all leading up to making fall 2021 the autumn of the Diana outfit.
Below, shop a few of Diana's most, well, Diana, looks, from her neon biker shorts to her collegiate apparel.
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."
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.
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.
It's not a Princess Diana spandex short outfit without a pair of white crew socks.
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.
August 1997
This 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.
Diana wore her sweatshirts baggy, often reaching mid-thigh. Make sure to size up for the same effortless look.
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.
Ray-Ban offers a modernized version of Diana's oval glasses with silver frames. We love this green and black iteration.
A large, purple Northwestern sweatshirt is the key component of this look. Find a near identical version here.
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.
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.
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.
Stars on top, stripes on the bottom, and cozy all over, Diana proved that flag-themed apparel is not just for July 4th.
Alo's biker shorts are often lauded for being both comfortable and flattering. A navy pair will complete your Diana-inspired look.
Like in her other ensembles, Diana paired this outfit with chunky white sneakers and white crew socks.
Though we're not exactly sure what a princess needs to carry, Diana brought along the most versatile handbag option—a classic black tote.
April 1997
Yet another USA item, Diana was not afraid to represent the nation across the pond.
Princess Polly's crewneck sweatshirt is nearly identical to Diana's. Size up to truly get that Princess Di oversized feel.
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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