Best Men's Boots for Winter

One pair has to cover the slushy commute, the weekend errand run, and dinner after. The Timberland Premium 6-Inch Waterproof Warm-Lined Boot makes sense when you want winter protection without giving up a classic look. Waterproof leather handles the wet part of winter, the faux shearling lining adds warmth, and anti-fatigue technology helps if you spend a lot of the day on your feet. Compared with the Columbia Men's Bugaboot III Boot, this one leans more toward everyday style than light, active comfort. It is not the boot we would pick if low weight is high on your list.

When the air hurts before you reach the car, warmth stops being a nice extra. The Columbia Men's Expeditionist Extreme Winter Boot is built for that kind of day, with OutDry™ waterproof construction, 400g insulation, and Omni-Heat™ Infinity thermal-reflective lining. Compared with the Timberland Premium 6-Inch Waterproof Warm-Lined Boot, this one is much more about deep cold than all-around style. It also brings a more built-up cold-weather approach than the Columbia Men's Bugaboot III Boot, which is the lighter, more active-minded option here. In mild winter weather, all that insulation can feel like more boot than you need.

Wet cold is its own kind of annoying. The Timberland Men's Chillberg Waterproof Insulated Boot goes after both parts with a waterproof membrane and 400 grams of PrimaLoft® insulation, so slush and raw temperatures do not ask your feet to pick one problem. Compared with the Columbia Men's Bugaboot III Boot, this one gives you a more insulated feel for ugly weather. Next to the Columbia Men's Expeditionist Extreme Winter Boot, it still reads as a serious cold-weather choice with waterproof protection at the center. The extra warmth comes with a heavier boot, which some people will notice by the end of the day.

Long walks change what matters. The Columbia Men's Bugaboot III Boot is the pair we would reach for when winter includes more movement, because Omni-Tech™ waterproof and breathable technology keeps weather out while staying breathable, lightweight insulation avoids that built-up feeling, and Techlite™ cushioning helps on pavement. Compared with the Timberland Men's Chillberg Waterproof Insulated Boot and Columbia Men's Expeditionist Extreme Winter Boot, this one gives up some of that heavier insulated feel in exchange for lighter comfort. It also feels more geared to active use than the Timberland Premium 6-Inch Waterproof Warm-Lined Boot. It will feel too light if you want the heaviest insulated option in the group.