It’s boot season, so put the sneakers aside and put on some man shoes, like these Cole Haan Air Morris Chukka’s ($140). Leather uppers, front lace-up with metal eyelets, leather lining, padded leather footbed, and NIKE Air technology in the sole.
Now that Summer is almost over, it’s time to put away the boat shoes and bring out your fall kicks. We suggest investing in a good pair of Clark’s Desert Boots ($75-$110). These classic Chukka boots can’t completely replace your shit-kickers, but those crepe soles hold their own on most type of terrain, and like all leather boots they only get better with age. They are a narrow fit, so make sure to order a half-size bigger.