If you don’t yet own a pair of chukka boots, Fossil’s Santino Leather Canvas Chukka ($118) would be the pair to buy. A sometimes strange hybrid of shoe and boot, the chukka has become a modern man’s staple for those times where neither a dress shoe nor a Nike is appropriate. This version combines waxed canvas and full-grain leather, avoiding the chukka flaw of often looking like a slipper or moccasin. Instead, these shoes are dressy enough for casual business attire but will go just as well with your winter plaid. The shoes have a rubber sole for quality comfort and a surprise plaid lining just for fun.