The current study presents a dynamic thermal model (DTM) which accounts for variation of liquid properties with temperature to predict the development of temperature pattern of the entire transformer for offshore wind application during energizing process. The DTM is benchmarked against dynamic heat run test which is applied on a natural ester filled transformer designed for offshore wind application. The transformer is equipped with fiber-optic sensors (FOS) to observe the temperature distribution of the winding and the liquid during heating up and cooling down processes. The investigations involve in-depth analysis of the thermal behavior of the winding and liquid at different locations to give physical interpretation of the dynamic thermal response of different transformer components during dynamic loading. The results are further validated with transient computational fluid dynamics (CFD) simulations. Eventually, the study gives guidelines and recommendations of dynamic loading of transformer filled with natural ester in cold climate.