With the prevalence of social media among women, online feminist movements are gaining momentum in Japan; yet their formation, development, and impact still need to be explored. This article studies #KuToo, an online feminist movement sparked by a tweet complaining about compulsory wearing of high heels in Japanese workplaces. By analyzing the cultural, media, and political factors behind #KuToo's development, this study explains how the movement is able to achieve online influence. Based on digital ethnography, participant observation, and semistructured in-depth interviews, three factors are found behind #KuToo's popularity: (1) its cultural resistance against patriarchal workplace norms based on shared personalized experiences of foot pain, (2) the formation of a loosely connected but functioning connective feminist community against a predominantly male backlash, and (3) an alliance with opposition political parties. Cross-reading Lance Bennett and Alexandra Segerberg's connective action theory and Pierre Bourdieu's discussion of habitus, this article argues that while #KuToo has created meaningful social connections to challenge high heels as a rigid workplace habitus through its cultural persuasiveness, media savvy, and political alliance, ample evidence shows that both #KuToo activists and supporters suffer from painful connections with an exploitative working culture, a violent social media backlash, and distant political parties.