This doctorate investigates portrait sculptures erected in Greece from the reign of the first Roman emperor Augustus at the end of the first century BC into late antiquity to ask how private individuals, in different ways, in different locales and contexts, brought Greek and Roman visual languages into conversation to situate themselves in history and within complex power dynamics. To explore what this sculpture did with, and contributed to, its Greek background, and, in consequence, how personal and local identities were expressed in actu and in situ, this thesis examines both male and female portraits. It brings together published and unpublished data from fieldwork undertaken in Rome, the centre of a unique multicultural Empire, and Athens, a hotspot of Greek intellectual activity in the Roman period. The thesis is structured around highly visible public contexts (temples, gymnasia, agorae, theatres) to examine the variables that affected modes of self-presentation in marble. It speaks not only to art historical concerns but, by virtue of its contribution to identity-studies, to questions of politics and class. The manifold expressions of local identities and the macro-identity of imperial Hellenism are mutually supportive in highlighting the problem of subjectivity and visual power in Roman Greece. Rather than cashing out portraits as unequivocally Greek or tokens of Romanization, this thesis understands portraiture as a powerful medium which shored up local elites’ currency and created common ground between Greece and Rome in tandem. This thesis investigates the ways in which local elite families developed their own sense of self around an eclectic version of Greekness, as well as how the act of looking at the portrait galleries of disparate spaces provided stimulus for the creation and structuring of a shared elite subjectivity.