The article explores the imperatives of postfeminism, specifically the dual mandates of what Shelley Budgeon (2011) calls “successful femininity”: self-invention and self-regulation. Using examples from contemporary American middlebrow fashion culture, it analyzes the way postfeminist ideology requires its subjects to fulfill these mandates by both following and breaking rules. Through this analysis, the article argues that a key feature of postfeminism is a detachment toward rules and those who follow them, which it traces to both an earlier feminist skepticism toward norms and a pronounced anxiety in middlebrow culture over femininity and individuality. It further argues that this detachment is an iteration of class privilege and is enacted through class violence, suggesting that postfeminism is above all a phenomenon of class as much as gender. Ultimately, the article argues that a postfeminist celebration of rule-breaking as a practice of successful femininity leads to inaccurate and dangerous notions of women’s agency, vividly exemplified in the figure of Sarah Palin, whose rogue affect both claims and disavows feminism.