Definitely one of Nike's boldest designs this season, the NSW Gaiter Boot is a technical model with clever functionality that's built for inclement conditions. The water-repellent boot features a rugged synthetic and leather upper that unzips for easy entry and an inner sleeve that features a slick lacing system that works by pulling a tab on the heel of the shoe to tighten the interior lacing for a more secure fit. 

$250, darksidesf.com