A classic trench boot is a very smart purchase this fall regardless of whether you intend to spend it in a fox hole or not. The Brown Trench Boot by Oak Street Boot Makers is a tribute to classic styling and American cobbling. This trench boot is designed not only to look good but with real practicality in mind. Horween leather and stacked soles will keep your feet dry, whilst the calf skin lining will ensure that your toes remain warm. A trench boot looks just as good with jeans, chinos or a smart trouser for when the commute gets snowy. $426 USD