Sperry Top-Sider Alpine Waterproof Boots

Who knew the boat shoe gurus at Sperry made boots? Your toesies will stay toasty in the Thinsulate-lined Alpine Waterproof Boots ($170). They're not half-bad to look at, either! Wear them with your sweet new winter coat and a knit hat and you've got yourself a Midwestern Chic outerwear look. We know, that's not a thing, but it should be. In our opinions, fashion could strive to be a little more comfy!

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