Every winter I think, “WHY DO I LIVE IN CHICAGO?” – and then the spring finally comes and I’m back to realizing that it’s my favorite place to be. I swear it’s going to be my last year (maybe I’ll move to California! Or South Carolina! Or some other warm place!), but the nice weather always sucks me back in. The truth is, Chicago winter isn’t that bad as long as you have the right winter clothes, and happen to have the best warm winter boots.

Now that I’m spending more time outside, walking Milo a bajillion times a day, this winter it’s more important than ever that I have super warm, comfy winter wear. I finally. buckled and bought a big down jacket (which I got on super sale at the Kate Spade outlet outside of Chicago!), but luckily I bought a few pairs of warm boots last winter that make for a much more manageable walk around Chicago on a snowy day.

Here’s a few of the best warm winter boots boots that are making  winter less miserable, and me slightly less likely to move out of Chicago.

The Best Warm Winter Boots to Survive a Chicago Winter

Shop My Warm Weather Boots Picks Below: (Refreshed for 2022!)

The boots I’m wearing in this post are the M. Gemi Alpi boots, that are unfortunately sold out – but I replaced them last year with these amazing Marc Fisher boots that I’ve been loving. They’re super warm and still have the same lace up style and they lasted pretty well through the Chicago winter! They probably have one more season of wear before I replace them – but it’s not too bad for a $200 pair of boots (not cheap, but $100 or less per season (if you take better care of your shoes than I do)) isn’t too bad.

Also, these photos are similarly from the archive (aka last year and I never got to posting them, whoops!). But I shot these at Park and Field when they had the patio all decked out for the holidays, and it was real pretty. I’m hoping I can go back and have some socially distanced holiday cocktails on the patio before the end of the year is over.