Boots to Wear and Repair Forever

Photograph by Tom Shierlitz

Shell out a few more bucks for the right footwear and you’ll get not only better-looking shoes, but ones that last longer with care, saving you money in the long run. Take the Dalton boots from Allen Edmonds. Aesthetically, they convey everything good lace-ups should: They’re trim (but not noticeably skinny) with rounded (but not awkwardly sharp) toes. Plus, their formal, wing-tip style is combined with the historically casual boot, so you can pair them with either jeans or a suit. And if your boss has a “boots are inappropriate” policy, just flash your soles. Seriously. After all, dress shoes are defined as having leather bottoms, and these calf-highs deliver on that front with leather soles and durable butyl rubber heels. We’ve worn our made-in-USA Daltons about once a week over the past 12 months, logging serious miles in the process. The bottoms remain intact, and the elegant walnut brown exteriors have won us compliments at everything from sales meetings to soccer games. As we enter the meat of our second winter in them, our feet couldn’t be happier – or more comfortable. [$375;]

For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!