Obviously, which boot you choose depends on your Winter climate and your current foot health. I looked for boots that are flat, flexible, have wide toe box with minimal to no toe spring. Not all of the boots meet all of the criteria, but at least they’re headed in the right direction. Also, it’s worth pointing out that not everyone is ready for a minimalist shoe. If you want to transition wisely to a minimal shoe, I recommend starting with Whole Body Barefoot: Transitioning Well to Minimal Footwear
by Katy Bowman.
Vivobarefoot Women’s Kula 
reported being flat, warm, flexible puncture-resistant sole, grip the ground and move as nature intended.
Vivobarefoot Women’s Karma Boot. As reported by someone who owns a pair: “The Karma is unbelievably comfy, but they do run a little small – as confirmed by other Amazon reviewers, too.” So, you might want to order a size up.
Vivobarefoot Women’s Gobi II Hi Top Faux Shearling Winter Boot Flat, flexible, feel the ground beneath you.
Minnetonka Boot Someday you will be mine, my sweet little moccasin boot. “I will find you…no matter how long it takes, no matter how far. I will find you.” — Daniel Day-Lewis to Cora, before jumping through the waterfall in The Last of the Mohicans. …Also said Barbara to the boot. Ok, these are a bit narrow, but I’m hoping they will stretch out since they’re suede. If you have tried them, please let me know.
Minnetonka Women’s Ankle Hi Tramper Boot looks
flexible but has a .5 inch heel and narrower toe box. It might work well for someone with a narrow foot who is transitioning to a flatter shoe. The report is that they are a tad wider than the Minnetonka boot listed above, but still on the narrow side. Ok, I know these may not be Winter boots to some, but again it depends on your climate.
Vivobarefoot Women’s Waterloo Rain Boot. These are cute, flat and flexible, but the toe box looks too narrow! I’m including them here in case you have a narrow foot.
Croc’s RainFloe Boots If you are looking for a rain boot with a wider toe box. These should work, even with your Correct Toes™. The downside is that it does have a little toe spring and a little heal elevation.
Croc Jaunt lightweight, flat sole and wide toe box
OTZ Troop Shearling Boot Wide toe box, zero drop, no toe spring and flexible! They are a little more pricey, but they are on my wishlist for sure!
Vivobarefoot Women’s Ella zero drop, flexible and wide toe box
Manitobah Mukluks Women’s Buffalo Dancer Snow Boot Vibram soles.
Columbia Women’s Minx When I buy shoes I look for a totally flat shoe (zero drop), flexible (lets my foot be a foot), no toe spring (shortens top of the foot) and most important to me is a wide toe box so my toes don’t get squished (leading to bunions and pronation). Rarely can I find all four qualities unless I buy minimalist shoes, but then I won’t get the good traction or warmth in the winter. These Columbia Minx offer warmth and traction, but the insole has about an inch high! The ball of the foot is about 1/4 inch, so my heel is elevated about the ball of my foot by 3/4 of an inch. If you take out the insole, these appear to be zero drop. They’re flexible even with the shoe liner and from what my friend who owns a pair says they get more flexible over time, which is a plus for me. There is a little toe spring (seems tough to avoid in most shoes). I can fit my feet in the boot while wearing my Correct Toes™ without squishing my feet, but just barely. They have just the right amount of room without the liners. Check out how they measure up to the shoe liner test (see below); I’m spilling over the edge a bit. Ideally, your foot should not spill over the edge of the liner. For reference, the widest part of my foot is 4 inches and I ordered the size 8 boot. I wish these were sold in wide or did not have a tapered toe. Pros: Warm (-25 degrees F), flexible, waterproof and zero drop without the liners, light, good traction. Cons: elevated heel, toe liner, a tad narrow, has a toe spring. Update: after a year of having these, I still love them. I’ve walked miles in them without discomfort.
Vivobarefoot Women’s Gobi II Hi Top Faux Shearling Winter Boot These are reported to be warm and are zero drop. The toe box is tapered but is reported to have a wide toe box.
Ugg Classic has a wide toe box (usually wide enough for wearing Correct Toes™), but has a 1/2 inch heel elevation.
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All the moccasin boots you posted are HORRIBLE for support, warmth, dryness, ECT. There is a reason we don’t wear them anymore. Lots of your other boots are good quality brands but style over comfort was not what I thought this blog was about.
As I mentioned in the article, your choice would depend on the climate you live in and your foot health. Not everyone needs support, a healthy foot supports itself. The reviews on the moccasin boots stated they are very comfortable and surprisingly warm.
I love my Minnetonka moccasin boots, but I don’t live in the tundra. Thanks for sharing the list-always good to keep track of what’s out there!
Thanks for the feedback on the Minnetonka! Year after year the list improves as the minimalist shoe movement is catching on.
FYI, OTZ shoes and boots come with rock solid, i.e., not flexible, cork insoles Sure, you can remove them–but the boots cost around $200, so, personally, I can’t see paying that much for what’s left of them minus such a substantial component. Might be nice if they’d offer a much lower-priced option without the insole.
Thank you for the info! I agree, the price is what is holding me back from buying these. I had thought the cork insoles were supposed to conform to the foot over time.
Conform to the foot, yes. Flexible, not in the slightest.
good to know. thank you.
Thank you so much for this list! I have been searching for months for a warm, not leather minimalist winter boot that would work with my vibram wearing toes. I bought the Columbia Women’s Minx and took out the insole – Perfect!! You made my winter so much better.
Thank you so much for this list! It’s great to see some options out there. I hope you update it this year too!
Everyone, please chavk out Softstar Shoes and Feelmax shoes. Truly barefoot, minimalist styles. Softstar is more for lifestyle, Feelmax offers technical athletic products. Additionally, Minnetonka offers soft sole moccasins that are great after you stretch out the toe box.
Thank you so much for this guide. I checked out every boot, ordered a few, and will send back the ones that don’t work. Zero drop really helps with my back problems, but I need extra cushioning too (I’m in my 60’s and need the shock absorption). Unfortunately, most zero drops are also minimalists. Altra makes nice zero drop shoes with good cushioning, but they don’t have a boot. I will experiment with extra padding in some of these boots and see if I can get a pair to work for me. Thank you again for doing the legwork on this.
I have the knee-high lace-up Minnetonka boot that you mentioned and I like it, but I do think that Minnetonka is too narrow, in general, in their footbed. I have a narrow foot so it isn’t terribly tight on me, but it really could use more room. I also had the ankle-high tramper boot from them and found it not quite as narrow but still snugger than I would like in a minimalist shoe. I have a pair of Vivobarefoot’s Ella boot coming in this week and am hoping those will suit me better since I love my Vivobarefoot running shoes.
Hi Dawn, Thank you for your feedback on the Minnetonka’s! How long have you been wearing them? Yes, they are too narrow for some. Have you tried stretching them out with shoe stretchers? I’ve also heard that you can put a baggie of water in shoes and put them in the freezer. The water will expand as it freezes and stretch out the shoe. Let me know what you think of the Vivobarefoot’s Ella boot.
There was a comment about the Otz shoes but I see they are no longer on your list. The espadrilles definitely have a stiff sole more like birkenstocks. But their other shoes are fantastic. I have several pairs. They have a wide toe box and nice flexible soles.
None of these can be worn to work as business attire or even business casual..is there really that big a gap in the market that nobody makes fashionable zero drop winter fare? ARGH! I’m a mobile examiner so am in and out of the car in all weather walking into client’s homes and offices. I can’t change shoes after I’m in their home….
For custom-made Moccasins and Mukluks made in Canada by First Nation
artisans using suede, moosehide, deerskin and bison hides, we can make
to order any colours including hand-beaded. Mens and womens and children’s
both. Earthing Moccasins in double soled deerskin and moosehide.
Several shades of hide custom fit.
Doesn’t get any more comfortable, naturally, that Moccasins.
No rubber (unless requested).
I love my Soft Star shoes; they have Women’s shoes normal enough for attorneys and other professionals. I’m more professional when I’m grounded and moving/walking naturally, effortlessly anyway. It is a different “look” that becomes normal and a vast improvement over falling forward and stomping in positive heels. I feel attractive in my five fingers shoes with an ankle strap and go dancing in them:)