The educational reproduction of elite masculinity in postcolonial societies has not been properly studied. This is partly because the postcolonial masculinities of non-western elites are accomplished through the cultivation of naturalized practices signifying the body politic of the nation-state. In Singapore, same-sex elite schools of colonial heritage, particularly Christian mission schools, play a central role in cultivating elite masculinity. Focusing on the elite Anglo-Chinese School, I analyze the array of class and racial anxieties displaced by the schooling of imperial white masculinity unto the decolonized field producing a middle-class Chineseness primed for the leadership of men. I also show that the masculinity is being transformed into a cosmopolitan masculinity co-opting maternal femininity, as the elites turn to engage neoliberal globalization. The case of Singapore shows the postcolonial adaptability of elite masculinities formed in the imperial era, achieved through the gender dynamics of resolving ethnic and class contradictions in elite schooling.