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To be fully grasped, the concept of sustainability needs to be brought to life through practical applications. Food represents an ideal starting point to examine the complexity of sustainability; the integration of dimensions such as nutrition, environment, society, and economics, and related perspectives, is fundamental for a sustainable transition. New transdisciplinary competences are needed to go beyond the state of the art. In this context, empathy and design thinking (DT) can effectively contribute in teaching sustainability of food systems. This chapter presents three case studies to test an innovative pedagogical model based on the coupling of DT with a systemic and empathic approach (including empathy toward yourself, toward others, and the whole planet). This proves to be effective in increasing both the understanding of the complexity of food sustainability and the agency of youth. Furthermore, the chapter presents recommendations for integrating such approach into food sustainability education.