Oak Street Oak Sole Trench Boot, $398
Ok, you got me: I am of the mind that brown is the one truly appropriate color for fall. But I will make an exception for this one: the Oak Sole Trench Boot in black from Chicago's famed Oak Street Bookmakers. It ticks all the right boxes: Horween leather, Goodyear welting, and a stacked leather, vibram-capped heel. And yes, fine, the black adds an enviable sleekness.
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