We wouldn't recommend actually attempting to cross a desert in them, but Clarks Desert Trek Boots ($100) are sure to add a touch of worldly flair to your look. These old-school, two-eye, ankle-length shoes feature a center-seam design, a roomy toe box that gives your piggies plenty of room to stretch out, and a genuine plantation crepe outsole for maximum comfort. For best results, pair with khakis, or cords.