Abstract: The object of this research is the process of transformation of individual characteristics and preferences of the participants of educational process in the conditions of Informatization of education. The subject of this research is the gender-stylistic peculiarities of students and pedagogues in the context of digitalization. Analysis is conducted on the gender aspects of educational process and gender differentiation trends. Special attention is given to the role of information technologies in achieving gender equality and importance of considering students’ stylistic orientation. The goal of this work is to determine the presence of gender differences and stylistic preferences of educational process participants within the framework of its Informatization and digitalization for development of ways of for considering individual preferences in organization and formation of learning environment. The stylistic profile of respondents was defined in accordance with the model of D. Kolb based on methodology of P. Honey and A. Mumford, adapted by the authors of the article. It included the questions specifying the stylistic orientation of students and pedagogues towards IT sphere. For quantitative assessment of manifestation of teaching styles was applied the method of semantic differential, which allows expressing the degree of agreement/disagreement with the proposed statement. The obtained data give a perspective on the peculiarities of formedness of stylistic preferences in acquisition of knowledge among the pedagogues and students on a gender basis. The more distinct gender differences in the teaching styles are revealed among the pedagogues, and their leveling is noticed among young generation. The dominant teaching styles for the majority of respondents became the ones of theoretical orientation (thinking and theoretical), which can be attributed to the impact of being engaged in IT sphere. The acquired results underline the need to draw attention to the absence of organic development of teaching styles of the students and allow determining further vectors of research – a comparative analysis of stylistic orientation of the participants of educational process based on age indicators.