Dermatological disease burden affects a large part of the population globally and requires significant efforts in improving our understanding and developing effective therapies. The complexity of human skin has always represented a major barrier to using adequate in vitro models and although major progress has been made in understanding the epidermal and immune components of the skin, other important fraction such as fibroblasts or the vasculature are understudied. Here we will discuss, the role of the vasculature in wounds and scarring, and describe the role of endothelial to mesenchymal transition as well as its molecular mechanisms driving a transcriptional rewiring of endothelial cells towards myofibroblasts.