This chapter uses the lens of feminine rhetorical style to examine how gendered expectations affect first ladies’ public speeches and how their rhetorical styles evolved over time. Selected speeches of first ladies from Eleanor Roosevelt to Melania Trump are analyzed and five recurring themes are reviewed. These include the discussion of feminine topics such as family and childcare and envisioning women’s role in society, addressing masculine issues such as war and politics through feminine rhetoric, connecting with audiences as peers, use of personal narratives, and use of expert sources and statistics. The chapter concludes that first ladies’ addresses are usually delivered within the bounds of stereotypical gendered expectations, though subtle deviations can be found depending on the first lady’s public image, her professional experience, and the popular opinion of the times. The analysis of first ladies’ rhetorical styles helps us better understand their evolving role in US politics.