This article considers the ideal of living simply, critically exploring the practical realisation that achieving simplicity in life is a complex and skill-laden business. Particular, localised versions of living simply are subject to consideration, centring on the lived experience of dwelling as exhibited in huts and bothies, a historic feature of contemporary rural landscapes in Scotland. The article considers the kinds of skilled practices associated with these built forms, and the embodied expertise understood by users and owners as emerging from time spent in simplified structures where modern conveniences do not come as standard. As such, it seeks to place skill within the 21st century but also question where skill is located physically, morally and imaginatively. In doing so, this discussion queries why a situated version of skill needs to be cast as personalised and place-based and subsequently introduces the adapted concept of a ‘skillscape’ after Ingold (2000).