This paper analyzes the discursive contestation among online news media about women in leadership roles within a Muslim majority society, Indonesia. Indonesian women have established a substantial leadership role in which the “ideal” modern woman has been the image of “wanita karir,” a commingling of various Indonesian feminist discourses and Western (post)feminist discursive formations. Despite the progress, women's leadership in Indonesia has recently been challenged by reactionary Islamist forces. Using a critical poststructural discourse perspective, we identify a range of four forms of femininity and female leadership in Indonesian online media that reside at the intersections of competing discourses. This paper offers two areas of contributions. First, we identify the leadership challenges faced by women in a South‐East Asian context, in particular within a democratic Muslim society like Indonesia. Second, we contribute to the theorization of women's leadership challenges from the perspective of femininity construction. In particular, we want to emphasize the notion of the multiplicity of discourses in shaping femininities. In doing so, we demonstrate the permutability, transformability, and adaptability of gender discrimination in our identified forms of femininity, and the limitations of the virtuous burden imposed by apparently supportive discourse.