ASK YOUR AVERAGE American man if he has any interest in Japanese fashion, and the answer may well be a cocked eyebrow and a shake of the head. That reaction isn’t unfounded. Thanks to the rule-shredding work of designers like Yohji Yamamoto and Comme des Garçons’ Rei Kawakubo, Japanese design has long had a reputation for being avant-garde.

But that’s just one facet of Japanese style. Since the 1960s, when the fashion-forward youth of Tokyo became enamored of the penny-loafered and blue-blazered look of American Ivy Leaguers,...