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.

Personally, I never owned Chelsea boots before my Vessi Classic Chelseas. Once they became part of my travel rotation, as well as my daily footwear, I pair them with everything from leggings to dresses and cool jeans. In this review, see why Dan and I are both so excited about them (they come in women’s as well as in men’s!) and why I think they’re the best investment for travelers.

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.

Truth be told, I’ve even worn them with shorts, if I’m dashing out of the house, and while they may look goofy, I don’t care: it’s the full-foot coverage and lightweight material that make them fine for beating the rain, even in summer heat. I wear them all times of year.

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 doofy in photos and have cringed when I look back. I wish I had brought shoes that looked better with my jeans, or with my dress. I’ve looked back on vacation photos and wanted to hide my eyes at how my running shoes were the only shoes I had taken and how weird they looked with what I was wearing.

With the Vessi Classic Chelsea boots though, this is solved. I even love how they look with a mini dress or a midi-style dress. I like how they look with wide leg cropped jeans, or straight-leg cuffed jeans. A Chelsea boot is timeless, and the Vessi ones are RAINPROOF!

Update for 2025: Despite having had my Classic Chelseas for two years now, they have held up amazingly. I think it’s probably for the best that I got them in Black, but I also picked them up in beige this year. They only have minimal fraying at the top, and it might be from brushing against my cropped pants. Other than that, the soles and waterproofing perform just like they did the first time I wore them outside.

First impressions and design details

When the Classic Chelsea boots arrived in the mail, I was kind of skeptic because I had just heard about Vessi. I was ready to adopt them, but had to give them a real spin first.

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 (the Weekend, Courtside sneaker, Tidal sneaker and I just got the Classic Chelsea in a second color!).

What makes the Classic Chelsea special

I think they’re the most special shoes I own. I never really considered that shoes could be “surprising” or could “perform” in different types of weather, so the Classic Chelsea has been an eye-opening experience for me.

• 100% waterproof protection Vessi’s patented rainproof technology keeps feet dry in any wet weather condition.
• Lightweight and breathable The design doesn’t feel like traditional rain boots, making them comfortable for all-day wear. They feel like boots with style.
• Sneaker-boot hybrid style The style works with everything from jeans and leggings to dresses, so it is perfect for versatile travel outfits. I have found few outfits that they do NOT work with.
• Vegan and PFAS-free Made from materials that align with sustainable travel values. They’re totally vegan with no leather components.

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.

I think part of cold weather travel is the humidity that makes feet feel colder than the air really is. With dry feet and the full coverage from a shoe like the Classic Chelsea, we’re nipping this in the bud: dry feet are warm feet, even in winter months and during cold-weather trips.

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.

I’ve tried quite a few styles from Vessi, though, and I’ve had varying rates of success in getting either 6 or 6.5, their newest half-size addition to only a few select styles. I have stuck with the 6.5 at times, and then for some other styles (the Tidal, the Courtside) I’ve gotten a 6, only to find that it is actually too small.

So to this point, Vessi’s sizing continues to perplex and surprise me but for the sake of talking about the Classic Chelseas, I wear a 6 and they are perfect for me (I wear a 6.5 sneaker in other brands).

To summarize, women should size down; but with men, go for your true size like Dan did (his size 10 is a fit).

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. No wet socks for me (that’s one of Vessi’s promises).

The water beads up on the surface of the Chelsea boots, 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 when wearing the Classic Chelsea boots from the Vessi women’s line.

Dan always wears his Chelsea boots (which look great on men) when it’s wet out in summer, spring or fall, to do chores outside or go out for errands. And we both trust our Classic Chelsea boots to be the only shoe we need if we take a day trip and some unfortunate dreary weather sets in.

Do I recommend them?

Oh my gosh, YES. I do recommend them and if you have the budget to put them into your travel wear, do it as soon as you can.

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.

This means I’M the person at the bar, on a rain-drenched night during the trip, whose feet are dry and whose leather footwear did not ger ruined. I am winning the all-types-of-weather trip conundrum. Bam!

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, which is fun. We’re exploring all the styles and continually staying dry. My Hunter rainboots even somehow had a hole, and I used to get wet socks despite the foolproof level of quality they’re supposed to have.

Vessi shoes have done us well, though, since the start.

Quick takeaways

• The Classic Chelsea is perfect for cool weather travel when you need waterproof protection, and they look stylish.
• 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 splashed in puddles, and my feet stayed completely dry.
• The unisex design means both men and women can enjoy the same style, just in different sizes. Dan and I both own them in black.
• Lightweight and breathable materials make these comfortable for all-day wear during travel. I also use them in all 4 seasons.

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. They’re exactly what I want when I’m packing light for travel and have to check all the boxes of unpredictable weather attire!

Comparison with similar products

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