May 21, 2024


Where Innovation Lives

The Princess Diana Athleisure Look Is Back Again

4 min read


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Welcome to the Season of the Princess Diana Uniform: We’re talking about the Princess of Wales’s go-to combination of an oversized sweatshirt, bike shorts, socks, and sneakers she wore generally on her way to the gym or while running errands. It was classic Diana (circa mid-’90s)—and it still makes the perfect outfit for transitional weather in spring or fall (aka before it gets too hot, or too cold). The outfit is so beloved, it’s become a celebrated meme that takes hold of fashion Instagram and TikTok every year.

@stringbeanboy13 bike shorts do be cute tho #fyp #foryoupage #nyc #princessdiana #foryoupage ♬ original sound – String bean

And for good reason. Bike shorts are an athleisure staple and warm-weather essential. They’re the shorter cousin of leggings, and just as versatile in function. (Take them to a workout class or pair ’em with a blazer for work.) But the real fun is pairing them with your sweater, socks, and, most importantly of all, sneakers, à la Princess Diana. This is the perfect outfit to really let your sneaks shine, so we’re taking the time to round up some of our favorite pairs that were truly meant to be worn with this ensemble. 

If you want in on the Princess Diana Uniform, here are some sneaker picks that’ll look royally awesome with your bike shorts and crew neck sweatshirts. 

Best sneakers to wear with bike shorts, Princess Diana style

new balance

New Balance® 996 Sneakers — $90.00

If you really want to go for the sneakers with the high crew socks look, there’s nothing better than these casual, old-school track style New Balance kicks to help you recreate that style. Not only are they on trend in the streetwear scene, but these sneaks will also help keep your feet comfortable all day long.



Nike air max Air Max 90 Training Shoe

Nike Air Max 90 Training Shoe — $130.00

If there’s one shoe you’ll likely see everywhere this summer, it’s the Nike Air Max 90 Training Shoe. They’ve become a staple in the sneakerhead community because of their super comfy fit and go-with-anything type design. Additionally, they have removable insoles in case you need better arch support.


Axel Arigato Marathon R-Trail Sneaker — $320.00

As far as trendy styles go, these chunky Axel Arigato Marathon R-Trail Sneaker are well worth the extra coins. Made with leather and with intricate web detailing, these sneaks are half comfort and half style. They have a removable cushioned footbed to support your tired feet as well as mesh lining for extra breathability.

Veja Venturi sneaker 2

Veja Venturi Sneakers — $180.00

Made from recycled polyester and other eco-friendly materials, these Veja sneakers are a win for both sustainability and style. Their pastel color makes them the perfect neutral shoe to pair with your warm spring looks from your neon bright bike shorts to your tailored trousers for work.


Adidas Ozweego Shoes — $110.00

If you want to show off your sneakerhead knowledge, these Adidas Ozweego Shoes are the perfect way to
make an impression on the masses. Their big and bold silhouette is a classic nod to the ’90s and ’00s sneaker era. Additionally, they’re a great pick for walking long distances because of their snug fit and special Adiprene cushioning that absorbs force and high impact.

Nike Air Max 270 — $160.00

Whether you plan on hitting the gym, or need comfortable—but stylish—travel shoe, these sneakers are ones that will offer all the support you need to stay comfortable. They’re designed to make your feet feel like they’re walking on a cloud. That’s thanks to their soft foam midsoles and mesh detailing throughout the shoe for better breathability.

Onitsuka Tiger Ultimate 81 — $80.00

These Onitsuka Tiger Ultimate 81 shoes are a classic throwback you’ll want to scoop up for your wardrobe. FYI, Onitsuka Tiger Ultimate 81 merged to become Asics back in 1949, but many shoes under the brand’s original name are still floating around (for example, on Zappos!). And these low-top kicks are ones that sneakerheads love thanks to their two-toned EVA midsole and heel that provides cushioning and flexibility.

Reebok Classic Leather shoes

Reebok Classic Leather Shoes — $80.00

If you’re hoping to follow in the footsteps of royalty (literally), these Reebok Classic Leather Shoes are another great way to go. A similar pair has been spotted on the Meghan Markle en route to yoga. However, we personally love them because of their sporty look that makes them easy to pair with other styles beyond bike shorts. For example, you can rock them with a maxi dress, or your fave pair of jeans.


Puma Cali Dream Pastel Women’s Sneakers — $90.00

Another one of the greats, Puma makes a great casual sneaker that’s stylish and functional. The marshmallow-gray colorways match everything you own while still feeling different from the rest of your all-white sneaker collection.


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Our editors independently select these products. Making a purchase through our links may earn Well+Good a commission.


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