Steven Tiller is a sneakerhead. Even though he’s spent his career surrounded by shoes—as a sneaker designer for Cole Haan, Lands’ End, Keds, and Steve Madden—he still marvels when he comes across an elegant, well-designed pair. In 2005, he was puttering around a vintage store in Tokyo when he came across an interesting pair of shoes in a glass case. They looked like a classic pair of blue lace-up sneakers from the 1960s—a more masculine version of Keds. Tiller didn’t recognize the...

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