Abstract: The subject of the research is the relationship between phenomenal manifestations of  transcendental will and gender. The author of the article provides the analysis of the concept of will in Kant's and Schopenhauer's works with the focus on the elements allowing to present will as an integral unit of the two modes, rational and irrational. The core of gender is the strategy of life as the balance of the two types of activity of personal identity – internal (development) and external (self-affirmation). The author of the article describes common features of these two modes, on the one hand, and associated life strategies, on the other hand. The definition of 'life strategy' is based on Hegel's dialectics of processes of objectivization (self-affirmation) and subjectivization (development). The author also offers a new approach to the definition of the concept of 'gender' not as a set of social roles of sex but a style, i.e. way of achieving super-goals that reflect this or that life strategy (in other words, gender is the answer to the question 'how' but not 'what'). The carried-out analysis of typical features of life strategies and will modes regarding their coincidence allows to prove that Kant was right relating rational will to the male strategy and irrational will to the female strategy. For the reason that the will shows the modes in each person, it is appropriate to say that there are both male and female beginnings in any man/woman, however, their balance is different. This circumstance allows to view the theory of Carl Jung as the method of a more detailed description of each will modes in a man. In the future the approach relating will modes to genders may allow to understand the mechanism of the mutual transition of will modes and features of time-space existence as well as preferences and connotations of axiological space and male/female lifeworlds.