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Boots

Boots

Buy It Now at Karmaloop, $240

When it's brick city outside, you need a pair of boots. Wheat Tims will never go out of style, but if you want to break apart from the pack, consider a pair of chunky-soled boots from brands like Danner or Red Wing. Rock them with cuffed denim, flannel shirt, and a beanie all winter long.

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