The 20 Best Winter Boots That You Won't Have to Break In

When it comes to winter boots, it's always hard to find a pair that checks off all the boxes—and that's the case when some simple pairs of water-resistant boots are more than enough, not even accounting for heavy-duty-boot climates. But the common denominator, no matter where you spend winter geographically, is that they have to be comfortable and stylish. Function and fashion need to go hand in hand when it comes to winter boots because there's nothing worse than taking your new shoes out for a spin and having your trip cut short because they still need to be broken in. Also, by mid-December, cold temperatures are the only things that need to be annoying you, not your boots, too.

That's why we've made it our mission to search high and low for the most comfortable winter boots on the market. From rubber Chelsea boots for those who live in areas where snow quickly becomes slush and heeled booties for those who still need a bit of height for some footwear flair to boots that feel like they’re hugging your feet in warm comfort with each step and chunky boots that don’t make you look awkward, the picks ahead can take a city, the countryside, or whatever Mother Nature throws at them without any Band-Aids needed.

Now go figure out the best winter socks to wear with all of them.