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This paper studies the structural types of comparisons and stylistic functions of comparisons, which are used in the portrait descriptions of heroes in short stories of A.P. Chehov. It's noticed in the paper that comparisons in portrait descriptions, which were written by A.P. Chehov, are multifunctional and have differences in structure. Comparisons are organized by different parts of speech: nouns, adjectives, verbs and verbalformations. It means that the method of including of different structural and grammar types ofcomparison into portrait descriptions is the particular technique of A. P. Chehov.