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I like boots for some conditions, but they aren't the only way to stay dry. In fact, for alot of hikes in my area (Southern Highlands) they cause as many problems as they solve. On an AT thru-hike, you can deal with snow drifts, standing water, and icy stream crossings in a few hours. Boots are awesome in the snow, but once you go through a stream they'll be wet until you build a fire or spend a night inside. Deep snow, snowshoes, shorter trips: go with boots for simplicity. For longer trips, I like a modular approach; it allows my footwear to match the conditions at the moment. The BPL articles on lightweight footwear for winter are a good primer:
http://www.backpackinglight.com/cgi-bin/backpackinglight/lightweight_footwear_systems_for_snow_travel_part_3.html
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