With the expansion of social media, clothed images adopt an increasingly significant role in disseminating complex, provocative, and ambiguous messages. Recently this ambiguity has been particularly evident with female politicians whose fashion choices produce a colorful, if not clear, atmosphere in which dress performs politically as "persuasive art." Indeed, it appears that ambiguity is intentionally embedded in the image-making process of these political leaders (Choy, 2015; Givhan, 2007; McNair, 2011). To consider our hypothesis, we examine images of Hillary Clinton, 2016 US Democratic Presidential Nominee, Angela Merkel, German Chancellor, and Theresa May, Great Britain’s Prime Minster. Our objects of analysis are items of dress culled from media images along with published articles. Our method follows Aspers’ (2001, 2006) phenomenological approach employing meaning structures with pertinent contrasts, reciprocal observations, and performance expectations. Although Beauvoir penned "The Ethics of Ambiguity in 1948," ambiguity has intrigued ancient philosophers like Aristotle ("Sophistical Refutations," 1984) as well as modern scholars like Simmel, Levine, and Butler. Little print, however, has been allotted to its intentional form. Thus, following Hebdige’s (1979) premise "style as intentional communication," we aim to fill this gap while extending aesthetic and media studies theory.