When can a good pair of boots make you look both sophisticated and rugged? Wear them with an ascot and carry a hunting rifle. No. Just throw on a pair of the ruggedly handsome Timberland Boot Company’s Tackhead 8-Inch Boots ($295). These beautifully unique two-tone boots are made from premium brushed Horween leather and treated organic canvas on top of a solid Vibram lug sole, making you look far tougher than you actually are. From Timberland’s high-end line of craft boots, the Tackheads will make you feel as if you’ve just disembarked a DeHaviland seaplane in the Alaskan wilderness, ready for adventure. Instead you’ve rolled out of bed late on a winter morning, run out of coffee and scrambled to get to Dean and Deluca before they start serving lunch. It’s okay. Your boots have “risky adventurer” written all over them.

Buy Now: $295