Historically, upwardly mobile working-class men have navigated the binary distinctions between a cerebral middle-class masculinity and a manual working-class masculinity. However, within an increasingly globalised world, the boundaries between the two are increasingly blurred and, therefore, distinctions between the two can often be quite complex. Part of the reason for this is the onset of post-industrialisation and increases in low-skilled service work which require certain facets of working-class masculinity to be readjusted. This conceptual article draws on existing historical and contemporary scholarship to delineate aspects of the borderlands between a working and middle-class manhood. We are interested in the identity work that occurs at the borderlands and what this may mean for upwardly mobile working-class men. The article acknowledges the role of sociological theory but instead foregrounds a social anthropological approach where we consider what the conceptual lens of liminality has to offer in light of historic and contemporary research.