27 Waterproof Shoes Under $100 That’ll Survive Rain, Snow, And Everything In Between This Winter

These are available with Amazon Prime’s Try Before You Buy!

I bought these a few weeks ago when my old pair of go-to black boots finally bit the dust after years of use. I wanted something a little more stylish and have always loved the look of classic Dr. Martens, but wasn’t ready to drop the money on them. Enter: these beauties. I’ve been wearing them all around NYC, and they haven’t hurt my feet one bit. I’ve also worn them in the pouring rain and my feet haven’t gotten the least bit wet. I love that they’ll go with practically all my winter outfits, and every friend I’ve worn these around have complimented them + asked where I got them (most people wouldn’t guess they’re from Amazon!). I got them in my normal size and they fit just fine, even with my thick winter socks. Highly recommend if you’re looking for your new staple boot!

Reviewers also compare the look of these to Prada’s lug sole Chelsea boots (which are over $1,000!). 

Promising review: “I took these boots to a trip to NYC, I walked all day and they did not cause any blister or extra tiredness. They are comfortable, easy to put on especially at airport security. They are so trendy and the platform is not tiring at all. They don’t claim to be waterproof but it rained a lot and my feet never got wet. I would definitely recommend these ❤️.” —Sandra

Get them from Amazon for $39.99+ (available in sizes 5–13 and 19 styles).