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This article explores Japan's entry into international commercial aviation in the wake of the Allied occupation with particular emphasis on its implications for female flight attendants' job duties and training. As Japanese aviation shifted from being a tool of empire for the military to a luxurious means of transportation for business, the newly established Japan Airlines (JAL) faced the challenge of fashioning an attractive brand for the American market. In 1953, in preparation for the launch of its first transpacific route from Tokyo to San Francisco, American advertising executives recommended that JAL design its corporate image around its "stewardesses" by dressing them in kimonos and foregrounding their personalized service. This rebranding strategy was intended to deflect perceptions of Japanese aviation away from the kamikaze and aggressive masculinity toward a performance of oriental femininity. This approach, however, ran contrary to the Japanese perception of "stewardess" as a modern, cutting-edge job for women. In order to compete with U.S. carriers, JAL's management saw the need to train its "stewardesses" to meet international standards of inflight service and engaged a "stewardess instructor" from United Airlines for this purpose. I argue that JAL "stewardesses" stood at the intersection of Japan's aspirations to modernity and the American imagination of the Orient, and that they learned to enact both, thereby assuming simultaneously a gendered yet paradoxically "modern" role in Japanese postwar aviation.