21 Comfortable Boots We’ve Actually Clomped Around In

With colder temperatures rapidly approaching, the time to invest in a pair of clompers is nigh. (Cool ones, of course — we use the term “clompers” lovingly.) We’ve watched a veritable parade of boots dance in front of our eyeballs like so many sugarplums — lug-soled ones, lace-up ones, low-heeled ones, chunky ones, knee-high ones, and faux croc stamped ones to name just a few. While all of these buckets are well and good, there’s one serious question that has the greatest effect on our decision-making process — but are they comfortable?

We on the Shopping team certainly have our opinions, but can only vouch for a few pairs among us. In an effort to give you a little more variety, we asked our fellow R29ers which comfy boots they swear by — and our stylish colleagues did not disappoint. They pointed out everything from a heavy-duty, tried-and-true heritage snow boot to a sleek, low-heeled, and pointy-toed number that will help elevate your WFH look five days a week. Click through to see which boots are really worth investing in this fall — with a high-comfort rating from people who actually wore them.