The Best Men’s Boots for Winter 2020

A sudden downpour or cold snap calls for weatherproof winter boots. Equipped with functional features like waterproof uppers, warm lining and thick, slip-proof soles, these boots can keep up with your warmest looks. So, go ahead and wear them with everything- from your go-to parka and jeans to a stylish Sherpa jacket with a lightweight puffer vest.

This season, dress boots are for more than just suits. Exhibit A: These statement-making pair of chain detailed boots, which will take you from fall to winter while elevating your everyday style. Add some edge to an all-black look, like a patent puffer jacket, high neck sweater and slim black jeans or channel a little rock with a leather jacket, white tee and stonewash denim.

Battle the elements while running errands in a modern-day combat boot. A sleek interpretation of standard military-style boots, this season’s lace-up boots are still plenty tough thanks to their rugged leather exteriors and treaded outsoles. They also happen to look just as great with a wool coat and suit as they do with a casual fleece jacket, half-zip sweater and dark wash, straight leg jeans.

For a slim-fitting alternative to classic winter boots, try a weather-treated take on the timeless Chelsea boot. Its sophisticated leather upper means you’ll always look pulled together—even in laid-back styles like a plaid jacket and blue jeans—while its rubber treaded sole will help with grip.