Because of its ability to treat many conditions, adipose tissue transplantation has become the core technique of regenerative medicine. Thus, it is receiving an increasing attention. This approach involves transplantation of fat rich in adipose-derived stem cells (ADSCs) and the by-product of processed lipoaspirate. Fat grafting is a candidate treatment for wounds, reconstructive surgery, and even metabolic disorders. But the complex relationship between donor tissue, recipient physiology, and transplantation itself demands a profound understanding of what the procedure involves before it can be established in the clinical routine. Deciphering the complex mechanisms of adipose tissue transplantation is greatly facilitated by both preclinical and clinical studies. In this way, based either on animal models or in vitro platforms, they both provide researchers with a controlled environment in which they can test variables such as graft survival and integration, angiogenesis, efficiency. In such models, implantation techniques can be improved, and their outcomes optimized to lay the foundation for successful clinical translation. This chapter covers the wider field of experimental models of adipose tissue transplantation. We review most utilized animal models and in vitro systems to highlight their advantages, shortcomings, and more importantly applications. Moreover, we are examining some of the relevant disease-specific models to explain how transplantation might affect conditions as obesity and protracted wound healing. Exploring advanced quantification and/or monitoring techniques, we show noninvasive approaches to observe and control the condition of transplanted tissues, as well as their degree of integration into the hostile environment. Lastly, we explore how these models can bring about changes and emphasize the link between experimental findings and practical applications in a clinical setting.