Gender aspects have been attracting linguistic attention for quite a while now, raising discussions about the so-called male and female languages. However, the effect of gender on translation remains understudied. This research featured expressive vocabulary in Jerome Salinger’s The Catcher in the Rye and its Russian translations performed by Rita Rait-Kovaleva (1960) and Maxim Nemtsov (2008). The objective was to determine the effect of gender on translation. The authors believe that the translator’s gender may affect literary images and modify the author’s message. They conducted a comparative analysis of the way translators of different genders transferred stylistically-marked and emotional vocabulary, colloquialisms, slang, and jargon into Russian. The standard methods of analysis, synthesis, comparison, generalization, systematization, and description revealed some differences in the translation styles, the image of the main character, translation pragmatics, and Salinger’s rather remarkable style. Rita Rait-Kovaleva seemed to soften some harsh statements, neutralize emotional aspects, and avoid colloquial vocabulary by using equivalents, which did not quite fall into the stylistic framework. Her Holden Caulfield turned out to more educated, intelligent, confident, emotional, and gentle. Maxim Nemtsov adhered to a single strategy: he did his best not to deviate from the original. In his attempt to preserve colloquialisms and substandard vocabulary, he often gave neutral words stylistic markers, emotional coloring, or a negative connotation. However, he managed to maintain the original syntax.