Numerous countries across the globe have witnessed the recent decades’ trend of multi-storey timber buildings on the rise, owing to advances in engineering sciences and timber construction technologies. Despite the growth and numerous advantages of timber construction, the global scale of multi-storey timber construction is still relatively low compared to reinforced concrete and steel construction. One of the reasons for a lower share of high-rise timber buildings lies in the complexity of their design, where the architectural design, the selection of a suitable structural system, and the energy efficiency concept strongly depend on the specific features of the location, particularly climate conditions, wind exposure, and seismic hazard. The aforementioned shows the need for a comprehensive study on existing multi-storey timber buildings, which correspond to the boundary conditions in a certain environment, to determine the suitability of such a construction in view of its adjustment to local contexts. Apart from exposing the problems and advantages of such construction, the current paper provides a brief overview of high-rise timber buildings in Europe. Moreover, it addresses the complexity of the design approach to multi-storey timber buildings in general. The second part of the paper highlights the importance of synthesising the architectural, energy, and structural solutions through a detailed analysis of three selected case studies. The findings of the paper provide an expanded view of knowledge of the design of tall timber buildings, which can significantly contribute to a greater and better exploitation of the potential of timber construction in Europe and elsewhere.