We have entered the season of cold weather scenarios when sturdy footwear is key. Luckily, there are no shortage of options . But, there's one boot like no other, ready for all types of terrain (not just the mountains, those city streets can be just as unpredictable), and that is the venerable hiking boot. However, that fine line between cute and functional can sometimes be thin. Whether you’re in the market for a pair that could work for a Cheryl Strayed -inspired adventure or something a little lighter that can get you around on a slushy night dressed in a leather mini skirt and tights, we've got a few options for you.