“Trendsetter” first ladies show new ways of modeling femininity in a given era, often through attention to the visual. Because women in public long have been expected to be seen and not heard, fashion and image historically have provided a way of communicating nonverbally. Thus, first ladies who were considered trendsetters typically circulated new “looks” or images to a given public, drawing from the culture in which they operated to influence norms around femininity, beauty, and celebrity. This chapter assesses seven first ladies for their visual influence. Dolley Madison (1809-1817), Julia Tyler (1844-1845), and Frances Cleveland (1886-89, 1893-97) were the most notable of the nineteenth-century first ladies who found themselves positioned as style icons. Following in their footsteps were Mamie Eisenhower (1952-1960), Jacqueline Kennedy (1960-1963), Nancy Reagan (1980-1988), and Michelle Obama (2008-2016), who each leveraged the trendsetter role during their time in the White House.