This article places under critical and reflexive examination the theoretical underpinnings of the concept of lifestyle migration. Developed to explain the migration of the relatively affluent in search of a better way of life, this concept draws attention to the role of lifestyle within migration, alongside understandings of migration as one stage within the ongoing lifestyle choices and trajectories of individual migrants. Through a focus on two paradigms that are currently at work within theorizations of this social phenomenon – individualization and mobilities – we evaluate their contribution to this flourishing field of research. In this way, we demonstrate the limitations and constraints of these for understanding lifestyle migration; engaging with long-standing debates around structure and agency to make a case for the recognition of history in understanding the pursuit of ‘a better way of life’; questioning the extent to which meaning is made through movement, and the politics and ethics of replacing migration with mobilities. Through this systematic consideration, we pave the way for re-invigorated theorizing on this topic, and the development of a critical sociology of lifestyle migration.