So-called “left behind” regions have gained infamy for working-class discontent. Yet a concurrent phenomenon has gone unremarked: middle-class lifestyles in peripheral places. This article examines how middle-class migrants (defined by economic, social, and cultural capital) to peripheral regions envisage and enact their aspirations. Against presumed migration trajectories to growing urban centres or for better-paid employment, we argue that seeming moves down the “escalator” reveal how inequalities between regions offer some migrants opportunities to enact middle-class lifestyles affordably. We present a qualitative case study of West Wales and the Valleys, predominantly rural and post-industrial and statistically among Europe's most deprived regions. Drawing from interviews with EU and UK in-migrants alongside long-term residents, we illustrate how three dimensions of quality of life—material, relational, subjective—are mobilised in middle-class placemaking amidst peripherality. We demonstrate how spatial inequalities and career trade-offs offer affordable material access to lifestyle and how middle-class aspirations enable migrants to subjectively transform peripherality into enchantment.