This article tackles the gender aspects of media tabloidization process, by empirical research on Estonian press and TV of the transition period 1990s-2000s. It shows, how media tabloidization/commercialization is gendered and how ambivalent is media's position in representing and reproducing gender order. Media, by tabloidization, legitimizes the shift of the gendered public-private borders in the society and from the other side, media acts as a maintaining factor of gender order as reproducing, producing and legitimizing patriarchal gender patterns. Discursive order, reproduced in media, clearly sets areas of expected expertize for both genders: everyday life, home, human relations for women; public issues, technology for men. Women are typically depicted in the context of or speak on TV on themes which Bourdieu called extensions of private sphere in the public. Media legitimizes gender order by representing this as a default division and it tackles separately exceptions from this division: by textual and visual means media constructs women in male-dominated areas as disturbance of gender order. Commercial pressures, fostering stereotypical images of women, accord with patriarchal frameworks of representing women. In Estonia as a postsoviet transition society, commercialization process is amplified by deep societal changes and value crisis, seen as a broader context for narrow and prejudiced representations of women. Increase in the number of women in media content that typically bring private issues into media, is influencing media intimization and personalization processes, and is seen as a result and also means of tabloidization. Democratizing potential of those representations is questioned.