Among the oldest shoemakers in England, Loake 1880 is still run today—five generations after its founding—by the Loake family. Like its founders did in the 19th century, the company still constructs each pair of shoes in its 1880 line using a Goodyear welt, a process that allows the shoes to be resoled. And the Kempton Chukkas are no different. Built on the round-toe 026 last, these Goodyear-welted boots feature a calfskin suede upper, three eyelets, and a rubber Dainite sole. Finished with a stacked heel, the Kemptons go as well with jeans and a flannel as they do with trousers and tweed.