The Red Hat Society (RHS) is a relatively new and international women’s network that offers "fun" and "friendship" specifically for women over fifty. Its members, the Red Hatters, are easily recognized in the streets by their red hats and otherwise purple attire, giving the RHS its unique flavor of leisure combined with expressive public performance. In this article, we use interviews and observations to study how the fun experiences aimed at by the RHS are articulated with negotiations of gender and age. Our analysis directed us toward a contradictory and multilayered expression of feminism and femininity entrenched in RHS performance. While some of the Red Hatters explicitly identified with feminism using RHS performance as a means to "undo" gender, others identified more with traditional femininity, using it to "do" gender instead. We introduce the concept of "radical femininity" to show how the Red Hatters continuously negotiate the volatile space between these two broad societal discourses that position women in contradictory ways. Furthermore, we show how Red Hatters draw upon fantasy as embodied in play to negotiate this space.