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Clarks Desert Boot. $150 at Clarks. If you're new to dress boots, start with classic chukka or Chelsea boots in either black or brown. Or take a look at our selection of the 12 best dress boots.

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Block heel isn't cushioned. Narrow toes. Clarks is known for being one of the most comfortable, durable shoe brands out there. Good news—they have a damn good leather Chelsea boot, with a.