Mr. Castleberry of Unabashedly Prep introduces Oak Street Bootmakers' new, blue Chromexcel beef roll penny loafer. He speaks with Oak Street's founder, George Vlagos, who explains that the shoes are hand-sewn in Maine, which apparently is the only region in the country where you can track down craftsmen still capable of the craft.

The loafers boast a stacked leather heel, welted construction (simply send them back to Oak Street for resoling), hand-stitched moccasin uppers, and carry just enough weight to intimate their craftsmanship.

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