Feels like a dumb question, but I haven't ever worn a pair of boots that didn't hurt in some way. Is this just a feature of boots, or am I doing something wrong?
I've always had Doc Martens boots for casual wear in the winter. They're really comfortable as long as you break them in by wearing them around the house for half an hour a day for a week or two before going outdoors with them.
I've only slipped over in my current pair once in 4 years or so - but I'm in the UK so winter boots for me are more about warmth and rain resistance than snow!