Vessi Courtside Classic Review: Vintage-Inspired Waterproof Sneakers for Travel

I am the type of traveler who likes to be highly prepared for a trip, and this means packing correctly for whatever the weather might bring. The Vessi Courtside Classic is a 90s-inspired waterproof sneaker that combines vintage aesthetics with modern waterproof technology.

And if that wasn’t enough to win me over, what really sold me on the Courtside Classic from Vessi was that they look good with jeans. You heard me right: one of my biggest style fears is now cured.

If you want to learn more about this travel shoe that gets me through daily outfit fears and unpredictable weather during my trips, read on.

What are they?

The Vessi Courtside Classic is a new type of shoe for me. Rather, I’ve been on the hunt for quite some time for a sneaker that I can bring traveling.

There’s a catch though: What about for those wet-weather destinations like Vancouver, Seattle and Ireland, where rain is a daily occurrence, and where ducking inside is not always a possibility? I say this because Dan and I did go to Vancouver, and we did get caught in daily rain, and once we even had to walk an hour in it because we were in a park. We got soaked.

There is a shoe that solves every issue, from style to function: the Vessi Courtside Classic. They remind me of good old sporting shoes, and they look great with jeans, leggings, sneakers and casual dresses.

And what do they do? They’re made with Vessi’s proprietary technology that makes water bead up and fall away, meaning they’re 100% rainproof. If I get caught in a storm, no worries: I’ll have socks that stay dry (which is Vessi’s main value proposition).

The Courtside Classics are cool shoes that come in both men’s and womens–now, in more fun color combinations than when they were first released–and they serve as a likeable daily sneaker that also braves the elements during wet weather travel.

Sizing and fit considerations

Here’s the thing: the Courtside Classic runs small compared to other Vessi styles. I wear a 6 in most of my Vessis, except for the Courtside, which was when I needed a 7. I’m working on the perfect Vessi fit!

Like I mention in my Vessi travel brand review, I really like Vessi shoes - a lot - but I just can’t figure out how they size the shoes in a nonstandard way. At least that is how I am experincing it. I’ve mostly lucked out with size 6 in their shoes, and the one time I ordered an available 6.5 half size–nope, it was the size 6 that I really needed.

Then, with the Tidal shoe, I ordered a 6, and nope: too tight. With the Courtside, a surprise again: I needed a 7. And in the Classic Chelsea, I happily wear a 6.

All in all, you can try to use the Vessi fit guide, which says to size down for more narrow feet, but you may have the same issues I did. All I can say is be prepared to potentially be exchanging for a size up or down, depending on how it goes for you, but in the end: you’ll be glad you got some Vessis.

What makes the Courtside Classic special

These vintage-cool shoes snag the win for sneakers that never look goofy, only polished. They go with everything, and might even turn heads and win compliments with the nice color comboes of white with a blue accent, or a light stone gray. In this quick list, see why they are unique:

• 100% waterproof Dyma-tex® technology that keeps feet dry in any weather condition
• Lightweight, cushioning midsole provides comfortable support for lots of walking while sightseeing abroad
• Soft and flexible gusseted tongue creates a tailored fit that moves with your foot, and allows flexible fitting
• 90s-inspired silhouette that’s timeless and pairs perfectly with travel outfits (so that I look good in photos!)
• Vegan materials no leather included, only 100% vegan fabrics and rubbers
• PFAS-free no “forever plastics.” That’s a win for me.

Quick takeaways

If you breezed over most of this review, the following list should give you a fair outline of what I mean to drive home in regard to the style, fit and function of the Vessi Courtside Classic.

• The Courtside Classic runs small - you may need to size up (shockingly, I did!)
• 100% waterproof protection that actually works (I tested them)
• 90s-inspired silhouette that’s timeless and versatile (believe it or not, they look amazing with jeans)
• Lightweight and comfortable for travel (you’ll only need to take 1 pair of shoes for packing!)
• Vegan and PFAS-free materials (better for the environment compared to most other brands)

The Vessi Courtside Classic is a great choice for travelers who want waterproof protection with a vintage-inspired style. I hope this review has helped you figure out if this is the style you want from Vessi, and if not, check out my Vessi shoe review for travelers to see the other style-forward options they sell.