Winter Boots for Walking

I don't just love these boots because they're named after me (fine, they probably weren't, but I still like the name). I love them because I took them out of the box and wore them all over Boston on a rainy day, and when I came home, I had dry feet, no blisters, and no foot fatigue. These ankle booties look great with jeans or dresses, and have just the perfect heel height (1 1/4") with a stability shank embedded into the midsole to provide excellent arch support and just enough lift. The buckle adjusts so you can customize the booties for a perfect fit. Rockport's Cobb Hill Carolines are totally waterproof, thanks to a seam-sealed construction and interior zipper design, so you too can wear them in the rain or snow.

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Not only are these faux fur lined boots super cozy, but they're also incredibly affordable, depending on which color and size you snag on Amazon. The Totes Cynthia are built for snow, but they're also very comfortable and easy to walk in.

It's really tough to find a men's boot that you can both commute in and not feel compelled to change out of once you're indoors. Rockport nails the comfort and fashion angle with its DresSports Luxe Waterproof Chukka. You can wear this on a business trip or to a nice dinner, and your feet won't suffer—the waterproof leather has a Hydro-Shield construction that will keep you dry even in a downpour, and the VIBRAM soles mean you won't slip. Even better, the boots have built-in Adidas sport technology for shock-absorption and cushioning to keep you comfortable.

Winter boots are the worst to pack—unless you're bringing Pakems. These boots, made for both men and women are lightweight and fold down flat (but are still insulated for warmth, and have a solid sole). Originally designed for skiers who want to ditch their heavy boots for apres-ski, Pakems are perfect for travel as well.

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These DailyShoes boots stretch all the way up to knee height to keep your legs warm and dry. Bonus: the zippered side storage pocket can hold your keys and cards while you're out in the snow.

Our tester Christine Sarkis raved about these boots in her review, writing: "Vibram’s Furoshiki Shearling High Boot is a wonderfully strange boot that does the impossible: It packs nearly flat…To transform them from flat-packing marvel to functional boot, you slip them on, then wrap your foot using two Velcro straps and then wrap the shaft of the boot around your leg and secure it with Velcro."

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Sketchers Performance On The Go Gleam Boots are ultra-lightweight, so they won't weigh you down or make your legs tired. A unique, squishy yoga mat insole makes these comfortable to walk in, and the faux fur lining will keep you from feeling the cold.

Men headed to cold and snowy environments will appreciate these boots by Northside. Built for outdoor activities, they're lined with Thermolite insulation for warmth without bulk. A removable felt liner with faux shearling collar can be called in on extra cold days. And with its D-ring lacing system, the Pack Boots are easy to take on and off at airport security.