Vivobarefoot's Porto is structured similarly to classic chukkas, but meant to be worn barefoot. With a puncture-resistant, thin rubber sole and unlined leather upper, the shoe is designed to allow your foot to move in its most natural state. But even if you're not a walk-around-barefoot kind of guy, the Porto's refined silhouette lets you look sharp without feeling formal. [Porto, $300, vivobarefoot.com]
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