The yarmulke is one of the most familiar external markers of Jewishness and also represents masculinity. This essay offers pertinent background information on the wearing of yarmulkes by Jewish men, including an overview of concepts of Jewish masculinity and the history of the gay Jewish community. The practice of wearing yarmulkes by gay men is critiqued, with particular attention given to the wearing of “pride yarmulkes” (those which are rainbow or otherwise supportive of the Lesbian Gay Bisexual Transgender (LGBT) community). This essay argues that head covering––especially through pride yarmulkes––takes on importance as a significant symbol in terms of self-identity and agency for gay Jewish men. Their use of yarmulkes demonstrates an affirmation of their Jewish identity at the same time as it broadens concepts of Jewish masculinity.