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Winner: Brooks Cascadia 4
The asymmetrical lacing system helps to create a snug fit for any foot, improving stability on all terrains. And its outsole is coated with a grippy silica, so you won't slip on slick or loose surfaces. "These shoes fit beautifully and have great cushioning. They truly feel like road shoes with killer traction," Kass says ($100, brooksrunning.com).