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11 Stylish Pairs of Men’s Boots to Get You Through Fall and Winter in Style

From chukkas to snow boots, there's a pair for every look and every weather forecast.

Boots from Diemme, John Lobb & Saint Laurent. Ssense, MyTheresa

What loafers are to the warmer months, boots are to fall and winter. Along with enveloping coats and swaddling sweaters, boots mark the changing of the seasons as accurately as any equinox. It’s not just a stylistic choice—these are shoes engineered to keep your soles cozy come rain, sleet, snow or polar vortex.

While a sleek pair of Chelsea boots are a wardrobe staple, hardier styles are designed to endure the most inclement weather. When shopping with the elements in mind, look for models with Goodyear welted soles (stitched in such a way to ensure water doesn’t seep in and lead your boots to an early retirement) and ultra-durable full-grain leather. But of course, we don’t all live in places with such seasonal concerns. If you’re in that lucky camp, there are even more options to be enjoyed year-round. We’ve selected 11 of the best pairs available now—from lightweight desert boots to rugged combat styles—for a guide to the boots that every man should have in his footwear arsenal.

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