If you need a good pair of winter boots, but aren't too fond of the bulk and weight typically associated with warmer footwear, you need a pair of Native Jimmy Duck Boots ($90). They've taken the familiar silhouette of the duck boot and modernized it, building it with lightweight EVA material and updated colorways. Choose from jiffy black, regatta blue, torch red, and beaver brown. Each pair is completely waterproof, washable so they're easy to keep clean, anti-microbial and odor-resistant so you don't have to worry about them getting nasty, and lined with micro fleece for warmth on even the coldest days.
Combining classic lace-up workwear style with the comfort of modern footwear technology, the Cole Haan Lunargrand Boot ($280) gives you everything you look for in a winter boot. Available in two understated colorways — brown leather or green leather with ripstop inlays — this boot features a waterproof leather upper perfect for keeping out snow and rain. A natural storm welt combined with EVA midsole and a rubber outsole provide additional protection against the elements. Nike Lunarlon cushioning in the sole gives you plenty of comfort, making this the ideal boot to wear all day.