Recreate Princess Diana’s Shorts and Sweatshirts Outfits


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It’s here. Those few weeks between summer and fall where you pull on your favorite crew-neck sweatshirt, a pair of spandex biker shorts, and ask yourself (as it’s become a TikTok trend), “Am I? … Princess Diana? ” It takes around two seconds when the beloved Princess of Wales’ favorite outfit makes sense – not warm enough to be sultry in a sweatshirt, but not so frigid to prevent bare legs. September is the prime time for Princess Diana’s outfit.

Lady Di has worn the look on several occasions, often on the way to or from the gym. The combination is simple: sweatshirt, biker shorts, crew socks, and chunky white sneakers (plus, often, his car keys). Over the past year or so, there has been a resurgence in style, as spandex shorts have returned to fashion, thanks to celebrities like Bella Hadid and Hailey Bieber. At the same time, sneakers have gotten bulkier, sweatshirts have gotten bigger, crew socks are replacing no-shows, all leading to making fall 2021 the fall of the Diana outfit.

Below, shop some of the more, well, Diana, looks of Diana, from her neon biker shorts to her varsity clothes.

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November 1995

The Princess of Wales has worn her Virgin Atlantic sweatshirt on several occasions. Diana’s coach once noted that she continued to wear the crewneck to diminish the value of paparazzi shots. Jenni Rivett recalls, “I remember one of her strategies was that she was going to wear the same Virgin sweatshirt every session.”

Princess Diana Fly Vintage Sweatshirt

An Etsy store sells a recreation of Diana’s Virgin Atlantic sweatshirt, which she has worn several times in her life. The sweatshirt was even auctioned off in 2019, of course, for a hefty price tag.

Spacedye Biker Shorts

While a navy sweatshirt and cream biker shorts might not be the most intuitive combination, the Princess of Wales illustrates that the two colors look even better together.

Hanes Women’s 6 Pair Comfort Seam Crew Socks

It’s not Princess Diana’s spandex cropped outfit without a pair of white socks.

Forum mid-high shoes

Diana’s high top sneakers may look all white, but they actually have a few black accents. These mid-top Adidas sneakers are of a similar style.

august 1997

This is perhaps the most famous of “Diana’s outfits”. The princess has remade her Harvard sweatshirt several times, usually paired with black spandex shorts and small circular glasses.

Champion Harvard University Crimson Classic Arch Crewneck Sweatshirt

Diana wore her loose sweatshirts, often reaching mid-thigh. Make sure to take size for the same effortless look.

Center Stage 6 ” Biker Shorts

The Bandier All Access Shorts are loved for a reason. You will definitely get a lot of wear and tear from this pair whether you recreate a Diana look or just slip them on for a workout.

OVAL @Collection

Ray-Ban offers a modernized version of Diana’s oval glasses with silver frames. We love this green and black iteration.


Continuing her penchant for college sweatshirts, Diana represented another American college, wearing a Northwestern sweatshirt and white shorts. Adding a bit of luxury, Diana accessorized it with a Gucci tote.

Northwestern Wildcats Crewneck Sweatshirt

A large purple Northwestern sweatshirt is the key to this look. Find an almost identical version here.

lululemon Align short 8 “

When you buy white spandex shorts, quality is key (you don’t want transparency issues). Lululemon’s Align Shorts are sure to provide acceptable opacity.

Gucci Diana medium tote bag

Diana’s handbag then received her name. The Gucci Diana tote is a classic and will go as well with work clothes as with leisure.

October 1994

Although Diana was, of course, British, she seemed to enjoy the novelty of the Americana-themed outfits, repeatedly wearing clothing adorned with the American flag.

Oversized Americana Sweatshirt for Women

Stars at the top, stripes at the bottom and cozy all over, Diana has proven that flag-themed clothing isn’t just July 4th.

High Waist Biker Shorts – True Navy

Alo’s biker shorts are often praised for being both comfortable and flattering. A navy blue pair will complete your Diana-inspired look.

New Balance NM1010

As in her other sets, Diana teamed this outfit with chunky white sneakers and white socks.

Classic tote in structured leather

While we don’t know exactly what a princess needs to carry, Diana brought up the most versatile handbag option – a classic black tote.

April 1997

Yet another element of the United States, Diana was unafraid to represent the nation across the pond.

USA Cream Crewneck Sweatshirt

Princess Polly’s crewneck sweatshirt is almost identical to Diana’s. Size up to really get that oversized Princess Di feel.

High Waist Biker Shorts – Neon Pink

For some reason, although many of Diana’s color combinations look unusual, they still work. For example, she teamed her red, white, and blue sweatshirt with fun neon pink bike shorts.

Round sunglasses for women, 53 mm

Complete the look with oval tortoiseshell sunglasses, like this effortlessly chic pair from Celine.

August 1994

Diana opted for contrast with her blue and orange-red outfit, but always opted for neutral accessories. Concrete example ? His white sneakers and tortoiseshell sunglasses.

Blue sweatshirt with small patches

An Acne Studios sweatshirt, featuring the brand’s logo, brings Diana’s blue sweater into 2021.

Billye Biker Shorts

Pair blue with a shade on the opposite side of the color wheel – an orange-red hue, as seen on Michael Stars’ biker shorts.

Double Club C Shoes

Why fix what is not broken? Diana, once again, went for big white kicks.

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