This dissertation is an investigation of elite men’s identities in later thirteenth- and early fourteenth-century Scotland, particularly as they pertain to categories of gender and ethnicity. During this timeframe, the Scottish kingdom experienced enormous political change, underwent geographic expansion, and, allegedly, a growing sense of ‘Scottishness.’ Beneath all of this, however, complex ethnic identities and attachments shaped the ways men interacted with the gendered expectations of their society. In the ways they acknowledged, refuted, or ignored these expectations, boys and men crafted identities that reflected the multiple, overlapping, and contradictory ideals and values socially inscribed on sexed bodies. In the medieval Scottish kingdom, the masculine identities of political elites, in particular, were created through negotiation between dominant and non-dominant masculinities forms, and were oriented toward and in relation to hegemonic masculinity. The subjects of this study represent the diversity present in the medieval kingdom, including members of the so-called ‘native’ Gaelic elite, more recent immigrants to the ‘feudalized’ heartland of the kingdom, and inhabitants of the western coast whose ancestry incorporated both Gaelic and Norse influences. These men engaged with gendered symbols of power and legitimacy across a variety of different cultures both within and outside the Scottish kingdom. The different ways in which they constructed, represented, and deployed their identities as masculine beings highlight the differences in how they negotiated between dominant and non-dominant forms, the shifting possession of capital and its meaning, and the contextuality of gendered experience. In bringing the relationship between gender and ethnicity to the fore, while drawing upon the work of R. W. Connell and Pierre Bourdieu, this dissertation offers a new way of considering the identities of medieval Scottish political elites.