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Here are all the characteristics that make a boot both a “dress boot” and a useful piece of cold-weather gear: Insulation from the ground (thick, multilayered soles) Inner insulation (warm lining, padding, etc.) – think moisture-wicking, traps heat in, and consider the thickness of the lining Waterproofing Wind/air resistance (non-porous material) Sole traction – leather soles are nice but rubber outsoles are the only answer Upper-ankle height or greater – ankle-height is more common; laced boots are generally considered dressiest,