In this article, we employ the theoretical framework and concepts of Pierre Bourdieu to examine the notion of “transition” from military to civilian life for U.K. Armed Forces personnel. We put Bourdieu’s concepts of habitus, capital, and field to work in highlighting key differences between military and civilian life. The use of social theory allows us to describe the cultural legacy of military life and how this may influence the post transition course of veterans’ lives. There may be positive and negative transition outcomes for service personnel when moving into civilian life, and by applying Bourdieu’s theoretical concepts, we explain how such outcomes can be understood. We suggest that the “rules” are different in military environments compared to civilian ones and that service personnel must navigate a complex cultural transition when moving between environments. There are numerous and significant implications—including policy applications—from understanding transition through a Bourdieusian lens, and these are highlighted throughout.