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Cap-Toe Boots
Allen Edmonds Bleeker Street, $385
This sleek, stylish ankle boot is handmade at the Allen Edmonds factory in Port Washington, Wisconsin, where they’ve been making high-quality mens shoes since 1922. The price tag is substantial, but you can wear them with almost anything, from jeans to slim-fitting chinos or a full-on suit. And they’ll last practically forever. Goodyear welted and handsewn, they’re eligible for the company’s “recrafting” service; for $125 every few years—or longer if you don’t wear them every day—you can send ‘em back to Allen Edmonds for a complete overhaul, including new soles, fresh welting and a nicely refinished upper.
Available at allenedmonds.com