The authors present an integrative account of how attachment insecurities relate to sexism. Two studies showed that attachment avoidance predisposes men to endorse hostile but to reject benevolent sexism (BS), whereas attachment anxiety predisposes men toward ambivalent (both hostile and benevolent) sexism. The authors also tested predicted mediators, finding that men’s social dominance orientation (a competitive intergroup ideology) mediated the avoidance to hostile sexism link. In addition, romanticism (an idealized interpersonal ideology) mediated attachment insecurity to BS links: (a) Avoidant men tended to reject romanticism (i.e., were cynical about romance) and, in turn, were likely to reject BS, whereas (b) anxious men tended to endorse romanticism (i.e., were idealistic about romance) and, in turn, likely to endorse BS. The authors conclude that men’s sexism stems in part from dispositional attachment working models, both directly and through the interpersonal and intergroup ideologies they generate.