The most iconic image that accompanied the 1996 publication of 20th Century Photography: Museum Ludwig, Cologne—and one that continues to intrigue scholars of black diasporic visual culture—was the German photographer Charlotte March’s black-and-white photograph Donyale Luna with Earrings (1966), shot for twen magazine. March’s subject—the African American fashion model and actress Donyale Luna (1945–79)—is of great historical significance, not only because Luna was the first internationally acclaimed black fashion model, but also because she had an especially arresting, black diasporic visage at a time of European American aesthetic hegemony in high fashion and limited opportunities for black visibility in the mass media. This article tracks the conceptualization of Charlotte March’s singular portrait of Donyale Luna, putting it in its broader historical context and, relatedly, as a pivotal image from a sequence of contiguous photographic statements and counterstatements by several of the leading fashion photographers from the Swinging Sixties. What this account points to is the often undertheorized role of race and gender in modern visual studies and, in particular, this picture’s implicit metanarrative of black female agency and civil rights–era cultural defiance. The social contract between the photographer and “the sitter” is also explored in this article, arguing that when the sitter is an imposing African American artist/performer/observer, the photographer—and by extension, the portrait’s audience—finds herself in the unique, deferential position of being in the sitter’s own metaphorical, critical purview.