5. Esatto's Classic Hiker $699 After years of working for Nike, David Smith, 47, launched Esatto in 2001 to create better-fitting hiking boots. While most mass-produced shoes are molded by machines, Smith makes each pair by hand, using full-grain leather. Smith works in Portland, Ore., but he sells mostly via mail-order, based on customers' foot measurements. www.esatto.biz
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