The global food system causes severe pressures on the environment. In response, farming approaches, such as regenerative agriculture, are heralded by industries and governments as mainstream solutions to keep the global food system within planetary boundaries. However, the absence of a clear scientific definition and the low level of consensus on science-based approaches to the monitoring and verification of regenerative agriculture has left many initiatives vulnerable to evidence-based allegations of greenwashing. Therefore, we first aimed to determine what is meant with regenerative agriculture. By conducting a global literature review we analyzed the level of convergence and divergence between definitions which resulted in the core themes of regenerative agriculture. From these core themes, we found that that soil conservation forms the basis of regenerative agriculture to regenerate and contribute to multiple ecosystem services. The core themes of regenerative agriculture, however, were found to be not equally relevant for every farming system and local context. For example, a dairy farmer on peat soil faces very different challenges compared to an arable farmer on a clay soil. Subsequently to a general definition, we aimed to make regenerative agriculture meaningful at the farm-level. We did this by creating a modelling framework that combines a soil model with a bio-economic farm model that quantifies the themes of regenerative agriculture and shows which regenrative objectives and practices are most relevant for farming systems in their local context. This modelling framework was applied to three contrasting farming systems in the Netherlands to determine if we can create tailor-made solutions for conventional farming systems towards regenerative agriculture. For these farming systems we showed that using regenerative practices improves environmental performance, but reduces farm profitability when using current business models. In order to further monitor the efficacy of implementing regenerative practices a comprehensive perspective on the role of metrics for regenerative agriculture is given. Here, we propose a flexible yet coherent framework for the transparent, temporal, and context-sensitive selection of metrics for monitoring the extent to which regenerative initiatives lead to verifiable changes in land management, and as such the degree to which they achieve regenerative goals. Overall, it is concluded that regenerative management can contribute positively to the transition towards sustainable food systems, however, an enabling environment for practitioners has yet to be established. This coming decade, we find ourselves at a unique crossroad where regenerative agriculture has the attention of farmers, citizens, industry, and policy makers alike. As such, we believe that this thesis contributes to the challenge of mainstreaming regenerative agriculture, thus securing a sustainable future for the land that humanity relies on for tomorrow's food and wellbeing.