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Winner: Timberland Lionshead
These sneaks are designed for even surfaces but supply enough traction to handle off-road detours as well. The rubber toe area protects against stubs on trails, while the flexible outsole and shock-absorbing midsole soften any stroll. "These fit me like a glove -- they have the perfect combo of cushion and support," Sidlar says ($110, timberland.com).