Your Winter Boot Checklist

Your Winter Boot Checklist
Your Winter Boot Checklist

There's something about this time of year that calls for more substantial footwear. You want something on your feet that can take on the unpredictable weather of the season. Even if you're blessed with a more temperate climate, you want a boot. And in late 2017 (as we prepare to enter 2018), that means you want a boot that's masculine and durable, with just a hint of heft. Thick-soled and sturdy, today's best styles toe the line between rugged work boots and the sophisticated dress versions you can easily wear into the office. They pair nicely with your tailored and cuffed flannel trousers but, of course, were made for beat-up denim or worn-in chinos. From proper slush-kickers and hikers to classic chukkas built to take on gnarly wet weather, here are the best buys for your money, no matter your budget.

Your Winter Boot Checklist

Thursday Boot Co.'s cap-toe Captain boots in olive suede.


Want a tough pair of boots that will tackle anything Mother Nature throws at them (while keeping your feet warm and dry)? These are for you.

Original Chippewa Rugged Boots

break-in time necessary

Original Chippewa, $279.95

Wolverine Rugged Boots

Wolverine, $199

Red Wing Rugged Boots

Red Wing, $260

The Rail Rugged Boots

The Rail, $120 / $89.90


Because you want some durable boots that can take on the weather while looking good with your favorite suit on meeting day.

Grenson Cap-Toe Boots

Grenson, $275


You don't need to camp or hike to take advantage of these comfortable boots with grippy soles and mountaineer details.

Moncler Hiker Boots

Moncler, $670

Timberland Hiker Boots

Timberland, $250

Frye Hiker Boots

Frye, $378

Greats Hiker Boots

Shearling lined tongue

Greats, $299

A.P.C. Hiker Boots

A.P.C., $545


If you don't have to worry about snow and slush, these are less extreme than the others above but still look seasonal.

Astorflex Chukka Boots

Astorflex, $145

Wolverine Chukka Boots

Wolverine, $180

Aquatalia Chukka Boots

Waterproof suede

Aquatalia, $395 / $276.50

Winterizing Primer

Even if you've got a sturdy pair of boots, you can't expect them to stand up to the winter's rage if you don't treat 'em right.