Recent scholarship has underlined the significance of costume with respect to self-representation in the Roman world in terms of both personal adornment and visual art. Discussions of the toga in particular often center on elite traditions, for it is their interests which drove both the history and the development of the toga. Yet the power of the toga as a marker of civic identity must have resonated especially with Roman freedmen, for whom it embodied not only citizenship, but also the restoration of legal personhood achieved through manumission. The ubiquity of the toga in the figural funerary monuments of Roman liberti underscores its significance in this regard. In the group reliefs, commissioned primarily by freedmen from the early first century BCE through the Augustan period, male subjects wear the toga almost exclusively. Furthermore, the overwhelming majority of men wear the sling toga, eschewing the contemporary toga exigua and more voluminous Augustan toga. Other scholars have attributed Roman freedmen’s preference of the sling toga to their generally conservative tastes in portraiture, evident also, for example, in their preference for veristic portraiture well into the Augustan period. However, other evidence suggests that such artistic anachronisms, whether used alone or alongside more contemporary elements of style or coiffeur, bore distinct ideological meanings in the context of the group reliefs. While all toga forms signified citizenship, Roman identity and ancestral tradition, those meanings were nuanced through the styling of the toga and the context in which it was worn. This paper considers how some Roman liberti employed the toga as part of their broader program of public self-representation. The visual evidence demonstrates that within the corpus of the group reliefs, the sling toga came to embody more than just civic and national identity. It stood for rigorous self-control and discipline, as well as the rejection of manual labor that was so intrinsically linked with servile status in Roman culture. Moreover, the rejection of the more fashionable Augustan toga in favor of the older sling toga demonstrates that Roman liberti were less interested in keeping up with the fashions of Rome’s aristocratic elite than either the elite themselves or contemporary scholars would have it. Instead of emulating elite models exclusively, the apparent conservatism of the group reliefs suggests that Roman freedmen engaged most actively with the monuments commissioned by their immediate peer group, other liberti of similar social and economic standing.