Many traditional regions are being transformed as industries restructure. Paradoxically, the global economic downturn offers opportunities to innovate on policies to regenerate areas experiencing deindustrialisation, with one emerging focus being the development of ‘green skills’ to facilitate the transition of these places to ‘green economies’. In this article, we explore similar policy objectives (i.e. regeneration activity based (in part) on green economy transitions) across three deindustrialising/deindustrialised regions – Appalachia (United States), Ruhr (Germany) and the Valleys (South Wales) – to provide an account of the ways in which different regions with similar industrial pasts diverge in their approach to moving towards greener futures. Our argument is that the emphasis in such transitions should be the creation of ‘decent’ jobs, with new economic activity and employment initiatives embracing a ‘high road’ (i.e. high skill/high pay/high quality) trajectory. Utilising a ‘varieties of capitalism’ analysis, we contend that an effective, socially inclusive and ‘high road’ transition is more likely to emerge within co-ordinated market economy contexts, for example, Germany, than within the liberal market economy contexts of, for example, the United States and United Kingdom. In identifying the critical success factors leading to ‘high road’ green economy, the implications for any such transition within the liberal market economy context of Australia are highlighted.