This article critically overviews the polemics between feminism and female/trans masculinities, examining the intersections of gender, race, class, sexuality, and generation inherent in the rifts. In doing so, this article illuminates various contradictions and dilemmas of feminist sex/gender theory recurring in butch/transphobia. Under the imperative of androgyny as a feminist ideal, butchness was regarded as a denial of one`s true lesbian self and "woman" identity and as unnatural role-playing. However, this accusation stemmed primarily from issues of class and generation; mainstream lesbian feminists were largely white and middle-class, and many of them viewed butchness as a working-class endeavor, and a practice of the previous generation. When radical feminism reclaimed female values and celebrated women`s culture, femaleness and femininity tended to be equated with feminist subjectivity. However, this article argues that all radical feminisms should not be reduced to gender essentialism. Many feminists understood a male/female role as a social construct, and the concept of "the woman-identified woman" also originally implied a feminist political position (women`s solidarity), not solely the display of a feminine gender. Nonetheless, in the condemnation of "male-identification," the assumption that female/trans masculinities are antithetical to feminism was maintained. Transphobic feminists criticize that transmen seek male privilege and internalize their own misogyny. Thus, they have worked long and hard to purge the existence of butch/trans feminists from feminist history. Transphobic feminists obscure their own cisgender (non-transgender) privileges and ignore transmen`s oppressions and disadvantages as a gender minority. This article offers that the challenges of female/trans masculinities need to be significantly reconsidered within feminism in order to reconfigure gender theory and move beyond gender essentialism predicated on the binary gender.