When it comes to side zip boots, men might shy away from their sleek and smooth style. However, anyone with their finger on the pulse of the runways knows that city boots are a major fashion staple for men this season. Knock offs are everywhere and the styles are both comfortable and chill. \n\nFor an overview of some of the best-looking zippered men’s boots on sale this year, read on. \n\n\n\nThe New York City Boot By Kenneth Cole ($220)\n\nDesigned by Kenneth Cole, this sleek city boot is all about its cool, grey leather. Break away from boring black with this unique boot that’s both smooth and sophisticated. \n\nThe biggest appeal of this particular boot is the lack of designs or embellishments. Free from buttons, clasps, buckles or stitching, the overall style is understated yet powerful. The best features are the non-slip heels – perfect for snowy or wet days. \n\nHugo Boss Ankle Boots ($175+)\n\nBoth fashionable and functional, these are a great pair of side zip boots. Men will love the rustic look of the dark and battered brown leather while women will flock to your understated style. The leather is handcrafted and the zipper made from aged brass, giving these boots a rugged and manly look. \n\nThese city boots are really made for the urban warrior – they can handle a beating during any winter storm, making them a pretty ideal choice for cold and snowy winters or stormy and wet springs. \n\nTimberland Zippered Walking Boots ($125+)\n\nThough stylish, Timberland boots are actually more about comfort than fashion. Designed with the Timberland Smart Comfort System, these boots are made for long hikes and afternoon treks, but are still stylish enough to wear out on the town. They even come with a waterproof guarantee for life to boot. The look is rugged and rustic, but still modern – making them a nice choice for winters in the city. \n\nCity Boots by Gucci ($560)\n\nFor a classy urban style, Gucci city boots offer an ankle-boot look with a comfortable, zip-up fit. Their cool, soft and comfortable leather look great with anything, particularly a pair of jeans. However, with a lofty price tag, you may want to keep them safe from blistery winter days or dark and murky puddles. \n\nFor side zip boots, men should look for boots that not only look good, but also fit well right off the bat. Unlike leather shoes, boots are less likely to stretch out, particularly around the ankles – which means finding the right perfect is crucial.