The Best Winter Boots

By Jess
23 Oct 2019
Jess Ann Kirby wears leather knee-high boots over jeans in the winter.
sorel slimpack riding boots / Despite the fact that i’m pictured wearing these in snow, they are more of a rain boot (which i discovered after wearing them in the snow).

Quite possibly the most asked about/requested topic ever in the history of this blog is (other than winter coats) “what are the best winter boots?” Well, how much time do you have? Truth is, I could go on for an abnormally long amount of time about winter boots, and I’ve been through MANY winters, 33 in fact (the one year we lived in LA we did not have a winter, and no LA, 50 degrees is not winter, sorry). I’ve also had MANY different pairs of winter boots, and currently own several so I do have some thoughts on the matter. Today I’m breaking down what are, in my opinion, the best winter boots, for every kind of weather. May your feet stay warm and dry all season long.

Fashion Winter Boots

These are your “I love winter but only when it’s sunny and there’s no wind boots.” A bit more fashion than function, these boots all have their pros, but they’re not going to help you shovel out your driveway or trek through 2 feet of snow. Sometimes you just want a good lookin, stylish boot for those winter days when there isn’t a pile of slush or snow on the ground.

  • I get so many questions about these boots. First let me say I LOVE THEM. I wear them a ton, but they have limitations. They are not a snow boot. Cold winter days, dog walks, hiking, shopping for your Christmas tree, yes, but trekking through snow, no. They fit tts, and I also love them in the black leather.
  • I’ve barely taken these off since I got them a few weeks ago. They are so cozy, warm and comfortable. They are waterproof, but more of a sneaker than a boot. Great for hikes, running errands and even rainy days. I recommend going up at least half a size, they run small and narrow.
  • A chelsea boot that’s waterproof. These booties have water resistant leather and waterproof rubber soles. Nisolo also focuses on ethical manufacturing and has a shoe recycling program. They come in a few other colors, the black leather is very chic too.

Rain/Light Snow Winter Boots

For those cold winter rainy, slushy days when you need to get to work with dry feet or run errands without submerging your foot in a puddle of street slush, these picks will do the job. The Everlane rain boots are a great year round pick for wet days in any kind of temps.

  • These are a great rain boot, super comfortable, a cushy foot bed and lots of traction. Wear them with boot socks and jeans or leggings or they look good with a sweater dress too. My only complaint is they can be a little tough to get off, not sure if it’s because I’m pregnant or if they’re just kinda tricky. I went with my true size.
  • I couldn’t do a winter boot round-up without the LL Bean Duck Boot. I will say I’ve worn these in the snow but I don’t find them warm enough. These are more your rugged, rainy day, muddy, slushy boots. If you need them for that, they’ll get the job done and you’ll have them forever, these last. Lots of reviews say to size down but I have my true size and they fit.
  • I got these last year and I wore them a ton. They actually do well in the snow and will keep your feet super toasty and dry but they’re not for anything too deep. These were my go to for dog walks when I just wanted to slip on something warm and easy. They have great traction too and the lining is so warm I went barefoot sometimes. I ordered my true size.

Cold Weather/Snow Winter Boots

These are your heavy duty snow boots, when you’re going on hikes, shoveling the driveway (who am I kidding Craig does this) headed to the mountains for a ski/snowboard weekend and everything in between. While I find these to be great picks for our typical New England winter weather (which don’t get me wrong is pretty brutal at times), if you’re looking for boots that will withstand the most harsh weather (thinking -10 degrees and below) you might want something more heavy duty, in which case good luck.

  • I’ve had these snow boots for years and they still look brand new. If you want to keep your feet super toasty and dry, these are your boots. I usually bring these when we go snowboarding to throw on after a day on the slopes. They’re great for pretty much any winter activity you throw at them and I like that they’re not super clunky. I went a half size up, for me they ran a little small.
  • I got these last year for my trip to Finland with Anthropologie. Every girl got to pick a snow boot and let me just say, I was the warmest. If you want something that will protect you from the elements these are it (I guess I should preface with the fact that usually the coldest days I’m going out on are in the teens and 20s not negative temps). My only complaint is these took some breaking in and rubbed a little on my heel at first. I went with my true size.
  • I actually don’t have these but I’m thinking about them for this winter. I don’t think I’ll be doing any trekking through heavy snow at 8/9 months pregnant in the middle of winter (or maybe I will) but I do still like my winter walks. These are waterproof, insulated and have a microfleece lining for extra warmth and if you want a great snow boot that’s not big and clunky this looks like it will do the job. Reviews say these run 1/2 size small.

Winter Boots

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  1. Kim wrote:

    My LLBean lined boots have lasted me years and they only look better with age. They are my go to for winter in New England! I find the sherpa lined ones to actually be pretty toasty with some wool socks. But they certainly aren’t knee deep snow boots! Thank you for this write up! Also, what jeans are you wearing in the field/camel coat photo?

    10.23.19 | Reply
  2. cate wrote:

    When I was doing my semester in college in Vermont I remember everyone was wearing LL Bean Duck Boots! now I need a pair XD

    Cate // 35mminstyle

    10.23.19 | Reply
  3. Joanna wrote:

    I love the looks of the Marc Fisher boot but after reading reviews and how they get the Shearling, I would not buy them. That is absolute brutal treatment of a two year old lamb, skinned before it’s slaughtered so we can have pretty boots. I had No

    10.23.19 | Reply
  4. Janee wrote:

    Thank you so much for this! I may be making a move from LA to Ithaca, NY in the next year and a half so that’s going to be quite the change for me! Glad to have some cute while also functional recommendations!

    10.23.19 | Reply
    • Jess wrote:

      That will be quite the change! Best of luck, you will definitely need ALL THE LAYERS. Haha. xx

      10.24.19 | Reply
  5. Rebecca wrote:

    Jess, do you have any suggestions for boot socks to wear with riding boots? I like when they just peek over the top of the boot under the knee, but I’m not having any luck finding a pair that I like.

    10.23.19 | Reply
  6. Rach wrote:

    Yes! Thank you for this post!! My mind is already starting to prepare for winter boots season and definitely need new ones!

    10.24.19 | Reply
  7. Meg wrote:

    AWESOME picks! I can vouch for the Sorel Winter Carnival boots in the bottom pic carousel in both slushy and extra-cold weather. I live in New England, but visit my parents in a frigid northern Hellscape each Xmas…they handle -25F, no problem; ditto nor’easters.

    10.25.19 | Reply
  8. Nicola wrote:


    Love the Nisolo Chelsea boot but they don’t ship to Canada :(.

    Any chance you know of any brands similar that ship outside of the states?

    Thank you!


    11.12.19 | Reply
  9. Alexa wrote:

    Loved the post! I’m curious if you could recommend any good water proofing spray as well? Amazon reviews are so polarising and a lot of them have a ton of chemicals – wish there was some green option for waterproofing boots!

    11.18.19 | Reply
    • Jess wrote:

      Thanks! That’s a great question, I haven’t found anything yet, but I need to do some testing, stay tuned.

      11.19.19 | Reply