Not sure where you live, but here in New England we've been blanketed in snow since December. And it's raining. I am constantly in and out of the house/car, and always cold. I need lots of layers and shoes I can slip on and off at the door (even though there isn't a speck of land to be seen under all that snow, yet we manage to track in more sand than the Sahara). My answer is lots of layers, and an easy slip on boot. And lots of time planning a tropical spring getaway.
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