Danner Arctic 600 Chelsea Boot / $200
It can be hard to find the right balance of durability, comfort, and style in a winter boot. Danner's Arctic 600 Chelsea nails it. It has a Vibram SPE midsole and removable OrthoLite footbed for comfort, a Vibram Nisqually Arctic Grip outsole for outstanding grip on snow and ice, and 200G of PrimaLoft Gold insulation paired with Danner Dry waterproofing to keep your feet warm. All of this is packed into a low-profile package that's just as suitable for the streets and it is for the trail.