Notwithstanding the increasing awareness of the gender approach to migration studies, research on how masculinity is entangled with mobility decisions, patterns and outcomes among highly-skilled migrants is still scant. This paper attempts to bridge this gap. By drawing on data derived from qualitative research, such as semi-structured in-depth interviews and observation, conducted among 75 Japanese classical musicians in France, Poland and Japan in 2012-2019, it probes the ways they negotiate their gender at and by work, moving between labour markets that have a disparate gender makeup and are unevenly positioned in the world order. Informed by Helma Lutz’s gendered model approach, the paper demonstrates that by heading off to France and to Poland, where, unlike in Japan, musicianship has long been considered an appropriate male profession, Japanese male artists seek to reinstate their gender by integrating into the local music world. In European music environments, however, these male musicians are unable to fully benefit from the privileges assigned to their gender because they are perceived primarily through their racialised ethnic identity. Thus, they again experience disadvantageous treatment, this time as ‘non-white’ musicians. Paradoxically, Japanese male artists make strategic use of this global asymmetrical, underprivileged positioning of Asian classical musicians to empower their gender identification. Namely, whenever they come back to Japan, they seek to defy their double marginalised masculinity by aligning themselves with the superior model of the Western music world, to which they belong as professionals. Thus, they endeavour to obtain the social status and prestige assigned to European musicians in Japan and to reposition their manliness on the Japanese gender map.