Sidewalk-tested boots that will keep city feet warm and stylish

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New York is a city that demands preparedness. You need to own jackets in a variety of weights and capacities for water resistance. You need a few different bags for different seasons and settings. And nothing could be more crucial than proper footwear, for walking in all the different weather the city can produce.

Fall and winter present the unique challenge of demanding footwear that repels water and cold without repelling your sense of style. Here are our favorite solutions to that New York problem.


Note: This story was originally published in 2017, but all prices have been updated as of January 2019.


When I was in high school, I wore Doc Martens steel toe lace ups with everything–dresses, jeans, miniskirts–you name it. I always enjoyed the power that came with a pair of clunky boots, like you could just kick the shinola out of anything, at anytime. Today there’s more reason than ever for power like that to be at my disposal. The classic Blundstone ($189) is a little more sleek than a Doc, but also has the humble history of a work boot. Blundstone, an Australian farming slip-on boot, feels right for all the hard work that we need to do. The perfect shoe for planting or protests, this boot has shock absorbers in the heel and technology in the toe for comfort. Mine also came with a packet of wax for weatherproof-ing, which means that I can be caught out in the rain, snow or sleet and never have to back down. Although when I first started wearing them, I got a terrible blister on my right heel, it didn’t take long for them to break in with thick socks. Wool socks are really perfect for although they keep my feet dry, they are not always warm. But they are a great winter go-to, empowering my feet to kick up a storm wherever I go. –Meredith Craig de Pietro


No. 6 Pull On Shearling Boot in Mid Heel

Oh, No. 6 Clog Boots, how I love thee. For six years, you have been warming my feet with shearling and leather, allowing me to walk all over town feeling as though I was only wearing slippers. You gave me just the right amount of height, and although you were only water repellent, somehow my feet were always dry unless I stood in a puddle. At first you felt tight on my toes, but eventually the padding wore down and I imprinted upon you. After the first winter, I wore you so much that the soles wore so far that I needed to get them replaced. By the following year, the salt and grime had scuffed the black toe to almost white, so I needed to get you polished. The next year the wood platforms had turned gray, and by the next year they were stained an almost black. This year, Old Clogger, I almost had to give you up. The shearling inside had worn so low that I could feel the nuts and bolts showing through the bottoms. You were no longer my comfortable, everyday boot, and I thought I would finally need to replace you. But then in Downtown Brooklyn, an elderly cobbler pulled out a brand new pair of shearling inserts. He also sewed back up some stitches that were coming out of the heel. But he trimmed those inserts to fit inside and I had to ram my foot inside to make it fit. My friend looked on in horror and asked me why I didn’t just get a new boot. I laughed at her ignorance. It took a few weeks of no socks for my feet to find their footprint again into the shearling, but now, Oh, No. 6 Clog Boots, you are almost as good as old. At $390, each year you become more cost effective, yet no money could ever replace the comfort you give me. I look forward to hopefully spending at least one more warm winter with you. –MCP


Sorel Slimshortie

You may associate Sorel with serious snow boots more suited to an arctic adventure than city streets, but I’m here to tell you that in recent years they’ve added some styles that really split the difference between fashion and function, for men and women alike. I’ve been sporting Slimshorties ($130) for four winters now and I still get compliments on them all the time. They’re not plunge into the slush puddle on the corner of Metropolitan and Graham waterproof, but they will keep your feet warm and dry on the street and toasty but not boiling at the office. Unfortunately, they’ve been discontinued, though you can find them on eBay, Poshmark and some discount sites with regularity.

I polled a few different friends whose footwear I admire, and every one of them had purchased and loved a pair of Sorel boots at some point, and there are lots of cute city boot choices on their website (though I stand firmly against a wedge or heel snowboot, that just doesn’t make any sense), and their comfort and durability comes vouched for.  —Annaliese Griffin

Dansko Maria

I will admit right now to being a clog junkie. I have three pairs of clog boots and a pair of “house clogs” that I wear around the kitchen, and that is a collection that was recently winnowed down. I find though, that for walking I don’t actually love a wooden sole on a clog. They make my arches tired and they’re really challenging on stairs and slippery environments. Which is why I wore these Marias from Dansko ($170) every day that I didn’t wear my Sorels last winer. The sole is some kind of polyurethane thing that flexes and they are so comfortable–I can wear these all day and walk miles in them. They’re not waterproof, but the sole and the nice lift they provide keep you out of the worst of it and the matte nubuck leather really hides scuffs and seems impervious to rain and puddles. Again, I wouldn’t wear these in a huge snowstorm, but for the day-to-day, slushy, gross winter streets of New York they’re super stable and more comfortable than you can imagine. They’re also a solid choice for anyone whose feet get overheated in insulated boots, and can’t be bothered with an office shoe and a street shoe. –AG

The Kodiak Alma comes in more colors than basic black. Buy every single shade. Photo: @unionjackboots

Kodiak Alma Boots

I always ask other women where they’ve bought their beautiful shoes or their great backpack that looks stylish enough to carry around outside of work. (Do you know of one? I’m still searching.) But I never went out and purchased the same exact item, until I spotted the Kodiak Alma on a friend. They looked so cool, and she spoke so highly of how warm and dry they kept her feet, that I got the same exact pair. And they were so great, and I got so many compliments, that I had no shame standing at the bus stop with her in the same boots, all winter long. Kodiak claims to have invented the world’s first waterproof leather, and wearing these does feel a little incongruous, as though you’ve slipped your feet into a warm, padded wetsuit. (Yes, I know that sounds odd, but it’s incredibly comfortable, so much so that I’ve gone out in them without socks.) Its black leather-on-wood style is like a dressier Blundstone, and it rings in slightly cheaper ($170 with free shipping from Kodiak, where you can choose from more shades, or $165 from REI Garage). As I head into a third season with them, I will say that their soles are perfectly intact but they could use a shine. It would also help if a certain puppy hadn’t chewed the top of one, but that didn’t prevent me from wearing them last year, so I will likely be sporting them again, bite marks and all. They also make equally good looking, and warmly waterproof, boots for men. –Nicole Davis

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