This fall, take a hike. While the urban woodsman schtick may not be quite as prominent, a good pair of attractive hiking boots never hurt anyone, or their feet for that matter. Many feature great padding on the insole, and that coveted Vibram sole menswear nerds hold in high regard. We love 'em with contrast laces, and suggest wearing them like you would any regular boot—no need to break out the flannel or hunting jacket—they pair just fine with a basic shirt, jeans or chinos. The D-ring detail on these boots add all the ruggedness you need, but the dark leather and details like suede trim really punch up the class. Here's a few in a variety of prices.
Contrast laces with D-ring hardware and a thick sole, exclusively for UO.
Made in Italy from water-resistant leather with antimicrobial lining and Vibram sole.
Removable insole with a suede and leather upper and rugged commando sole.
Gore-tex lined, recraftable and made in Portland for Danner's Stumptown collection.