This paper presents an analysis of Gogol's short stories "The Overcoat" (1842) and "Diary of a Madman" (1935) as well as the analysis of Dostoevsky's novel Poor Folk (1946). The main character in each of these three texts is a titular counselor, a clerk who was a recurrent theme in Russian literature. Each text reveals the functionality of the costume and contains a large number of clothes motives that hide a specific meaning. The aim of this paper is to analyze the distribution of costume roles in three texts written in different genres and in different narrative forms, and to analyze the possible evolution of the social function of clothes motive. In the short stories "The Overcoat" and "Diary of a Madman" evolution of clothes' social function is expressed by transforming the old clothes into a new ideal costume that has an utterly functional significance. When achieving a new status of the king of Spain, the main character of the story "Diary of a Madman", Poprishchin, creates a new costume that fits social standards and complements its (fictional) social role. The main character of the "The Overcoat", Bashmachkin, changes his costume even twice and finally he gets the ideal general's overcoat. On the other hand, Devushkin, the main character of the novel Poor folk, is going through a spiritual evolution which is expressed through his perception of the costume and the material world in general. Each motive in the novel was used to express his thoughts and understanding of the social world. At the end of the novel he throws his costume away and he reaches the level of spiritual liberation. The hero is trying to respond to the social standards and norms, and the environment that significantly affects his thinking and self-awareness creates an unnatural man. Each of the three heroes in the end experiences some sort of "(un)happy awakening" and "nudity" which is opposed to the costume and the illusion they lived before.