
It’s almost spring time–which means it’s Princess Diana Workout Look . . . Time! If that’s a thing. It’s a thing, right? That time where it’s not super cold, not super warm. Where you need to bundle up kinda but want to feel the breeze on your legs. A season to wear sneakers . . . with a high end designer bag, because why not?! If you want to rock the Princess Diana Activewear this spring, here’s a few ideas on how to do just that.
The Original Princess Diana Workout Formula

The Princess Diana Workout formula has been talked about and replicated many a time, so I’m doing a slightly updated version for today. But first let’s start with the basics of the look. For the traditional version of the look, here’s what you’ll need:
- An oversized sweatshirt, preferably with a large, vintage-y logo (Billabong Ride In Sweatshirt, $65)
- Retro style white sneakers with a colorful accent (Nike Free Metcon 4, $120)
- Classic black wayfarer sunglasses (Ray-Ban New Wayfarer Color Mix Sunglasses, $201)
- Oversized un-gym-like tote bag (Madewell Sydney Tote, $138)
- White or brightly colored bike shorts (Old Navy Extra High-Waisted PowerChill Biker Shorts, $19.99)
- Chunky white tube socks (Urban Outfitters Chunky Athletic Knit Crew Socks, $9)
A New Take on the Princess Diana Workout Look

The original Princess Diana workout look has been around for some time, and I want to do my updated take on it to make it a bit more modern. Whether you’re wearing this to workout or run errands, I think the Princess Diana vibe is perfect for Spring and early Fall. Here’s my take on an updated Princess Diana look for the early 2020’s. It’s all about upping the color and making the look slightly more practical for modern life.
Here are the choices I made to update this lewk:
- I love the idea of wearing a bodysuit instead of just bike shorts. If you’re going to the gym for real, it makes it easy to take off your sweater and have a proper workout outfit on underneath. (Old Navy PowerChill Cami Bodysuit, $34.99)
- Honestly, I saw these late 90s style sunglasses in Target yesterday and just loved them. They still have the square look of the Wayfarers but with a 90s shape and lime green color. (Wild Fable Crystal Square Sunglasses, $12)
- Colorful socks–spice it up a bit. White tube socks are what your dad wears. Plus Bombas are literally the most comfortable socks known to man–you heard it here first. (Bombas Disney The Little Mermaid Calf Socks, $19)
- Let’s face it, a tote to the gym is not very practical. But I didn’t want to go totally practical so I still kept a backpack in an unpractical material of leather. (Madewell The Lorimer Backpack, $228)
- I updated the oversized sweatshirt with an option that puts the huge print on the back instead of the front, because why not? (Billabong I Am Grateful Fleece Sweatshirt, $41)
- And just to tone it down a bit, I went for all white sneakers. (ADIDAS Ultraboost Sneakers $123)
Why This Look Works
I have a few key takeaways of why this look works after thirty years. Now, of course, Diana wasn’t the only person to wear this look, but she definitely is well remembered for it.
- It works on many body types.
- You always look like you were just working out, even if you weren’t.
- The fancy purse makes it look like you just popped into the gym after a lunch date or work.
- The classic sunglasses add an air of mysteriousness–who is she? Why is she wearing a fancy purse to the gym?
I hope you enjoyed this look and happy spring! (Or fall)
Shop the Post

ADIDAS Ultraboost Sneakers

Billabong I Am Grateful Fleece Sweatshirt





Urban Outfitters Chunky Athletic Knit Crew Socks

Old Navy Extra High-Waisted PowerChill Biker Shorts

Madewell Sydney Tote


Nike Free Metcon 4
