$100, by New Balance
If you passed on a pair of hiking boots back in the fall, this hybrid may be the perfect compromise. New Balance's 710 hiker will take you through the harsh stretch of winter, the warmer, wetter days of spring and into summer. This lightweight shoe is inspired by the brand's Rainier model, developed by famed mountaineer Lou Whittaker (at right, wearing the first pair). After an injury forced him out of his boots, he took to climbing mountains in New Balances and soon became a collaborator with the brand. The 710 has been relaunched a few times over the decades, but this year the classic version is available—crafted from English leather and hearty nylon with heavy-duty cotton laces. (There's also a more monochromatic option in sandy suede). Perfectly suited for cuffed jeans, cords or even some dark flannel trousers, the retro shoes will keep you grounded wherever you end up.