Fashion is closely related to the main values and trends of society development because it is a complex socio-cultural phenomenon, a mechanism of social and cultural regulation. Modern digital transformations determine the fashion development vector, contribute to the emergence and assertion of new values, change behavioral strategies. So fashion issues, its functioning and forecasting trends mechanisms become a topic of particular relevance. This article analyzes the values and trends of fashionable behavior. Based on the analysis of existing theoretical approaches to the study of fashion, the authors reveal some features of the modern process of constructing representations about fashion. The results show that the qualitative and quantitative development of information technology infrastructure comes to the forefront. Social media form a certain way of life, creating benchmarks of fashionable behavior, not excluding the diversity of variations and interpretations, taking into account differences in social status and in the system of value orientations.Based on the analysis of in-depth interviews, the key values of fashionable behavior originating from modern social media, have been determined: equality, tolerance, gender neutrality, active social position, environmental friendliness, naturalness. Content analysis of the messages content on the topic of fashion and fashionable behavior (published on various social media, using an automatic media monitoring system and Social Media Medialogy) allowed to identify the main thematically similar clusters reflecting fashionable behavior: healthy lifestyle, ostentatious consumption, avoiding excesses, environmentally conscious behavior, body positivity. The main trends in fashionable behavior originating from social media are: maintaining the relevance of ostentatious consumption, the transition to environmentally conscious consumption, body attitude change (“body positivity”). Fashion is closely related to the main values and trends of society development because it is a complex socio-cultural phenomenon, mechanism of social and cultural regulation. Modern digital transformations define the fashion development vector, contribute to the emergence and assertion of new values, change behavioral strategies. So fashion issues, its functioning and forecasting trends mechanisms become a topic of particular relevance. This article analyses values and trends of the fashionable behavior. The features of the modern process of fashion ideas construction are revealed, based on the analysis of existing theoretical methods to the study of fashion and the fashionable behavior. The results show that the qualitative and quantitative development of information technology infrastructure comes to the forefront. Social media is becoming the main source of the fashion values and the fashionable behavior. Social media is shaping a certain way of life, creating standards of the fashionable behavior. Thus, it does not exclude a variety of interpretations and takes into account differences in social status and in the system of value orientations. Based on the analysis of in-depth interviews, the key values of the fashionable behavior, broadcast by modern social media, have been determined: equality, tolerance, gender neutrality, active social position, environmental friendliness, naturalness. Content analysis of the messages content on the topic of fashion and fashionable behavior (published on various social media, using an automatic media monitoring system and Social Media Medialogy) allowed to identify the main thematically similar clusters reflecting the fashionable behavior: healthy lifestyle, ostentatious consumption, avoiding excesses, environmentally conscious behavior, bodypositive. The main trends in the fashionable behavior broadcast by social media are: maintaining the relevance of ostentatious consumption, the transition to environmentally conscious consumption, body attitude change (“bodypositive”).