DEARBORN, MICHIGAN is pretty far from Tokyo—home base for designer Junya Watanabe. Over 6,400 miles in fact. Yet Mr. Watanabe has long cherished one of Dearborn’s most famous exports: a brown canvas Carhartt work jacket (aka chore or barn jacket). “Carhartt appeals to me because it makes real and authentic workwear,” he wrote in an email. For a while now Mr. Watanabe has been reconfiguring actual Carhartt jackets, reusing them to make original pieces for his 17-year-old brand. This season in particular, he went wild with Carhartt riffs, adding patches, extending the jackets’ length and breaking them in to achieve that...