I’d be more concerned about slippery soles if I thought I’d be walking in rain, snow, slush, and/or ice. Over the years, I’ve favored Blundstones, Fryes, sturdy leather walking shoes, trail runners, and hiking boots which have all served me well in places as diverse as Toronto, the Yukon, the PNW, mountain towns, and the Maritimes.
Instead of buying footwear you are unlikely to wear for more than a week once a year, waterproof a leather shoe or boot that has a grippy walking sole, pack a couple of pairs of wool socks, and toss in a set of gaiters if you think you might be slogging through deep snow or slush. A set of gaiters takes next to no room in your luggage and (unless you are into fancy mountaineering styles) are usually under $40–much cheaper than any decent snow boot. A pair of gaiters work better at keeping my lower leg and feet dry in snow and slush than any snow boot I’ve ever owned, last for decades, and can be worn with almost any style boot or shoe.
