7 Desert Boots That Can Survive the Winter

Every product was carefully curated by an Esquire editor. We may earn a commission from these links. Here’s how we test products and why you should trust us.SeaVees/Thursday Boot Co/SabahThese 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.They’re very comfortable thanks to a soft, leather lining on the inside and open-cell foam insoles that provide supportive cushioning. And the flexible outsoles made from XL Extralight injection molding are a nice touch that give the boot some lightweight flexibility.ColorsDark brown, cinnamon brown, blackSizes6.5-15Upper MaterialEuropean calfskin leather (for dark brown and black colorways)Outsole MaterialXL Extralight injection moldingFor a classic pair of chukka boots that come at a good price and have a wide range of colors and sizes, Thursday Boot Co. is the way to go. These chukkas come in a variety of colors and materials, but our favorite has to be the Mocha colorway in weather-safe suede. It’s rare to find a pair of suede shoes you can actually get wet without ruining, but these ones can brave the weather while still looking great. And with studded rubber outsoles, you have some extra traction and durability. If you want even more traction and durability in the soles, try one of the Rugged & Resilient styles with anti-slip wedge rubber outsoles.Colors7Sizes6-16Upper MaterialWeatherSafe Suede (for Mocha colorway)Outsole MaterialRubberAdvertisement - Continue Reading BelowHere’s another suede option you can actually wear during the winter; Sabah treats the suede upper of this boot to be water resistant, but you can still add a suede treatment for extra protection if you want to. These boots are handmade in Monte San Giusto, Italy, and you can trust that they were made with lots of skill and care. The insole and midsole are made from vegetable tanned leather, so they end up forming to your feet once you wear them, making them extra comfortable.Colors5Sizes5.5-15.5Upper MaterialWater-resistant suedeOutsole MaterialRubberIf you like the look of a gum-sole sneaker, you might like how it looks on a boot, too. With these desert boots, SeaVees blends the classic gum-sole look with the more rugged desert boot style, and the result is a versatile boot that can withstand pretty much any weather. With water-resistant rugged oiled leather uppers and natural rubber soles, these guys can get you through quite a lot.Colors4Sizes7-16Upper MaterialWater-resistant rugged oiled leatherOutsole MaterialRecycled natural rubberAdvertisement - Continue Reading BelowThese are going to be the least weather-ready on this list. You don’t want to take them out in a snowstorm, but damn do they look good. Imagine these worn to a holiday party, worn with a nice pair of chinos and fair-isle sweater.The suede upper is a true not-water-resistant suede. But they do have durable rubber soles. The stitched moc-toe is a fun detail that makes these chukka boots stand out from the rest of the pack. Drake’s notes that these boots run small, so they recommend sizing up by a half-size when ordering online.ColorsLight brown, dark brownSizes5.5-13Upper MaterialSuedeOutsole MaterialRubberWe’re starting to get pretty far away from the chukka heart, but you can see the chukka-shaped vamp and the ankle-y shape. Plus, when we think of rugged workwear boots, we think of Timberland. The upper is made from waterproof leather and has a TimberDry waterproof membrane for extra protection, and you can see that Gripstick rubber outsole gives you some distance from the ground and provides great traction as well.ColorsBrown, blackSizes7-15Upper MaterialWaterproof Premium Timberland leatherOutsole MaterialGripstick rubberAdvertisement - Continue Reading BelowAnd finally, we can’t talk about chukka boots without mentioning Clarks. The original Clarks desert boot was designed in 1949 and inspired by the rough suede and crepe-soled boots worn by off-duty British soldiers during WWII (as well as the shoes worn by polo players in India and South African veldskoen shoes). Today, the brand’s original style is still going strong, and you can get a pair for under $100.Colors5Sizes7-15Upper MaterialWaxed leatherOutsole MaterialRubber