Converse, $175
We'll just start off by saying that these aren't for everyone. But for guys who want some tough (yet comfortable) kicks to tackle the winter conditions, these hybrid hikers do the job and then some. They offer the durability and traction of a hiking boot with comfort and casualness of a tennis shoe. And they'll easily take you through the harsh stretch of winter to the warmer, wetter days of spring. From Converse's suede hightop with a Vibram sole to the archival styles by New Balance and the North Face, these retro shoes are perfectly suited for cuffed jeans, cords and even some dark flannel trousers at times. Consider them the modern man's snow shoes.
The North Face, $110
New Balance, $110 / $90
SeaVees, $158 / $126
Nike, $80 / $68
Timberland, $90
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