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7 Desert Boots That Can Survive the Winter

7 Desert Boots That Can Survive the Winter

esquire.com 06.11.2026 15:54 17 views
Despite the name, these chukkas are built to be worn in all conditions.

If it’s not wind and rain, it’s slushy sidewalks and unexpected snow flurries. You obviously need shoes that can handle a little precipitation, but the key phrase here is a little. You don’t want to stomp around in heavy winter boots, especially if we want to look nice.

Dress shoes are a tough fit in winter, as are dress boots. Funny enough, between December and March, you know what our go-to footwear becomes? Technically chukka boots, but a few desert boots make the cut here.

But that’s something to note. The Esquire office does not use the term interchangeably—but the Internet does, so we’re going along with it. We know some of you—nerds, mostly—have stopped reading this article because you don’t think we know the difference between the two.

We’re well aware of the square and rectangle-ism: All desert boots are chukkas, not all chukkas are desert boots. If you’re not a nerd and want to learn something new, chukkas are ankle-high boots with open lacing and two or three pairs of eyelets, often made with leather uppers—leather or rubber soled. Desert boots are a subsection of this silhouette that typically features a suede upper (nubuck, sometimes) with lighter-colored, more flexible crepe soles.

They are not as winterized—suede, especially, is known to take a beating from moisture—hence the name. The details vary here and there, but both styles can work for winter if you choose wisely. We found seven pairs of chukka boots—yes, some of which are desert boots—with weather-friendly features, from water-resistant uppers to sturdy rubber soles.

Most have both, so you can find a pair that looks sharp without leaving you entirely at the mercy of the winter weather forecast. These chukka boots might as well be dress boots. They look sharp no matter what outfit you pair them with, and the ultra-refined, premium calfskin leather upper is naturally water-resistant; to a point, that is—we wouldn’t wear them in the pouring rain.

Extract — continue reading at the source.

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