The article highlights the importance of the architectural drawing in the modern education process presented by classical monuments of the past. Nowadays architectural practice raises the issue of evaluating the artistic merits of a unique drawing being considered in view of actualizing and presenting new computer technologies, digital technique. The need to evaluate the classical architectural legacy, which beneficially influences the modern architects minds and the formation of their professional culture. This aspect highlights the problem of a lack of culture compared with classical epochs. Therefore, the unalterable role of academic teaching in the XVIII-XIX centuries as the strong foundation of professional skill, is noted. Combining the art skills of the past with a modern perception of the world is an important issue of continuity being the key and universal one for creativity as a whole. Defining the essence of the problem and its relevance, the authors of the article note the necessity of prioritizing in teaching the architectural craft. Qualitative changes to the lifestyle of a modern human have lead to the changes in their point of view on the modern drawing and the architecture when stylistic epochs were replaced by modern movement’s architecture. In this regard, the issue of the dialogue between the "old" and the "new" schools has become a trend of time. Creating a new architecture requires architectural science, which should incorporate drawing in synthesis with other fields of knowledge. The analytical method used in the article assists to identify the acuteness of the given problem and its actuality at the current stage of creativity and the prospects for its solution.