Sperry Shoes CUTWATER REALTREE OLIVE – Review
ReviewSperry Cutwater Deck Boot Chelsea: Making a Splash in Style (and Staying Dry Doing It)
Alright, let’s dive into the Sperry Cutwater Deck Boot Chelsea. You know I’ve always had a soft spot for Sperry’s classic boat shoes, right? So, when I saw these – a tougher, weather-ready cousin of the original – my curiosity was definitely piqued. I recently got to kick the tires on these boots, and here’s what I found.
First Impressions:

Right out of the box, these boots just look good. Seriously, they’ve got more style than your run-of-the-mill rain boot, and that Chelsea boot design? Total versatility. I went with the olive color myself; I think they rock with everything from jeans to chinos.
Performance: From Deck to… Dirt?
Okay, so I don’t exactly have a yacht parked out back (one day!), but I do find myself around water a fair bit. Just the other weekend, I was helping a buddy with some serious yard work, and these boots were a godsend. That non-marking rubber outsole with the fancy Razor-Cut Wave-Siping thing? It works. I felt rock-solid walking on slick pavers and through muddy patches. And get this: I even got caught in a sudden downpour, and my feet stayed bone-dry. Plus, the heel pull? Made kicking them off at the door a breeze when I inevitably tracked mud inside.
Comfort and Fit: A Few Tweaks for Perfection
That removable EVA footbed gives you a decent bit of cushion, but I’m gonna be real with you, I threw in my own insole for some extra support under the arch. If you’re planning on logging some serious hours in these, I’d suggest you do the same. The neoprene upper dries fast, which is awesome, but I did notice a little rubbing around my ankles when I went sockless. Trust me on this one: wear socks! As for sizing, I’m usually a 10, and these fit like they were made for me.
A Couple of Things to Keep in Mind:
While the construction seems pretty solid, I do wonder how long that sole will hold up if you’re pounding the pavement day in and day out. Also, these aren’t built for deep-sea diving, folks. Water’s gonna sneak in over the ankle if you get too ambitious.
The Bottom Line:
All in all, the Sperry Cutwater Deck Boot Chelsea is a great pick if you need a stylish and practical boot for wet weather or messing around near the water. They’re comfy, they grip like crazy, and they look sharp. Just keep those potential downsides in mind, and maybe grab some extra insoles for good measure.
My Rating: 4 out of 5 stars.
Who Should Buy These Boots?
- Anyone who needs waterproof footwear for boating, fishing, gardening, or just surviving a rainy commute.
- Anyone who wants a rain boot that doesn’t look like a rain boot.
Who Might Want to Skip These?
- Anyone planning on wading through waist-deep rivers.
- Anyone who needs a super-durable boot for seriously tough jobs.
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