These outdoor boots could definitely be rocked with a pair of khakis or distressed designer jeans. The Red Wing Heritage Wacouta Boots feature a high top silhouette that pays homage to the original moccasin-style boot of the mid-2000s. (Speaking of paying homage, the Red Wing Heritage Wacouta Boots gets their name from the Wacouta Township where the Red Wing family has owned a cabin for three generations.)

Ready to wear as you walk confidently through oil-slicked city puddles or stroll down a dirt road in Napa Valley, the hydrophobic waxed canvas will keep your feet and ankles dry. Stitchdown construction adds an aesthetically pleasing bit of flair, while the brass eyelet hardware creates a rugged first impression. The Vibram Honeywheat Mini-lug outsole softens the boots, making them equally at home traversing the worn boards of a log cabin or stepping out of the plush interior of an Aston Martin.