Vessi Classic Chelsea Review: Waterproof Comfort for Cool Weather 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 Classic Chelsea is a waterproof sneaker-boot hybrid that combines the comfort of a sneaker with the coverage and style of a boot. Dan and I both own these shoes, and they’ve become our go-to winter footwear.

Why I chose the Classic Chelsea

I opted for the Vessi Weekend Chelsea shoes because they look good. I have tested them in outfits with dresses, jean shorts, leggings, pants and joggers. I find that they’re super easy to slide on and off, and they go with mostly anything.

What I like to avoid, in choosing which shoes I take on a trip, is ones that look bad in photos. That’s because I’ve been there. I’ve looked back on vacation photos and cringed at how my running shoes were the only shoes I had taken and how weird they looked with what I was wearing.

First impressions and design details

When the Classic Chelsea boots arrived, I was immediately impressed by their sleek, minimalist design. Unlike traditional rain boots that look bulky and utilitarian, these have a sophisticated silhouette that works well with both casual and slightly dressier outfits.

The ankle coverage provides just enough warmth for cool mornings without being too heavy for warmer afternoons. The elastic side panels make them easy to slip on and off, which is convenient when going through airport security or quickly changing shoes in hotel rooms.

Real-world testing in cool weather

The waterproof protection was equally impressive. We walked through puddles that would have soaked my regular sneakers, and my feet stayed completely dry. The water beaded up on the surface and rolled right off, just like the other Vessi styles I’ve tried.

What makes the Classic Chelsea special

• 100% waterproof protection with Vessi’s patented Dyma-tex® technology that keeps feet dry in any weather condition.
• Lightweight and breathable design that doesn’t feel like traditional rain boots, making them comfortable for all-day wear.
• Sneaker-boot hybrid style that works with everything from jeans and leggings to dresses, perfect for versatile travel outfits.
• Vegan and PFAS-free materials that align with sustainable travel values.

Perfect for cool weather travel

The Classic Chelsea has become my go-to shoe for fall and winter trips because it handles the unpredictable weather that comes with shoulder season travel. What I love most is how these shoes look good in photos while still being practical. I can wear them to dinner with a nice pair of jeans or pair them with leggings for a casual day of exploring. The ankle coverage provides just enough warmth for cool mornings without being too heavy for warmer afternoons.

Dan appreciates that they’re unisex - the same style works for both of us, just in different sizes. He’s been wearing his with everything from joggers to chinos, and they’ve held up great through daily wear.

Sizing and fit details

So, here is how sizing went for me. I ordered a Women’s 7 the for my first Vessi shoes (the Weekend Chelsea). They were gigantic. I wondered if they were supposed to run that big. I went through Vessi’s exchange process to get a size 6, and those are the Vessi shoes I wear at least twice a week.

Waterproof performance in detail

The waterproof protection uses the same Dyma-tex® technology as other Vessi styles, and it performs flawlessly. I’ve tested these in everything from light mist to heavy downpours, and my feet have stayed completely dry every time.

The water beads up on the surface and rolls right off, which is satisfying to watch and reassuring to know that the protection is working. I’ve walked through puddles that would have soaked my regular sneakers, and my feet stayed completely dry.

Do I recommend them?

Here’s what I love: as a favorite experience with Vessi shoes, I like how the Weekend Chelsea shoes can double as a “relaxed boot” to wear out to dinner or to a bar, if paired with nice jeans or a dress. They’re kind of like pull-on casual boots that live a few different lives. And of course, they’re waterproof.

Dan has gotten into wearing his Weekend Chelsea shoes all the time, too. He also has them in black. We’ve started a Vessi collection.

Quick takeaways

• The Classic Chelsea is perfect for cool weather travel when you need waterproof protection without sacrificing style.
• The sneaker-boot hybrid design works with a wide variety of outfits, making it versatile for different travel activities.
• Vessi’s waterproof technology actually works - I’ve tested it in real rain and my feet stayed completely dry.
• The unisex design means both men and women can enjoy the same style, just in different sizes.
• Lightweight and breathable materials make these comfortable for all-day wear during travel.

The Vessi Classic Chelsea has become an essential part of my cool weather travel wardrobe. It’s the kind of shoe that solves multiple problems at once - weather protection, style, and comfort - which is exactly what you want when packing light for travel.