There are many factors that influence the way readers perceive classic literature, which accounts for the importance of reading classics from the perspective of contemporary cultural concepts. In this article, we analyze Nikolai Gogol’s short story “The Overcoat” and examine the multi-level organization of the text and its layers of meaning from the perspective of a modern reader who is accustomed to a worldview that emphasizes personal responsibility for one’s interactions with the world and their own destiny. At the same time, the idea of the existence of the unconscious, various methods of psychological defense, etc., have become widespread in the mass consciousness being part of the cultural code. In other words, the new context has a significant impact on the reader’s perception of a classic work, which determines the novelty and relevance of the research. As a result of our research, we found that the narrative in Gogol’s work is organized at two levels: the external and the internal. It is easier for a modern reader to reach the internal level than it was for the writer’s contemporaries. We traced the contrast between the reader’s perception of the external events, described in the story (the image of the main character is distinguished by absolute archetypal coherence, it is difficult not to “recognize” a holy righteous man with a bitter fate in Bashmachkin and not to feel pity for this character), and reflection: gradually the reader would discover a number of contradictions in the story of Akaki Akakievich and, solving the author’s riddle, would move from the story of a little man in the best literary traditions (including the traditions of ancient Russian literature, depicting similar images in the genre of hagiography) to a metaphysical and philosophical level.