The notion of femininity, in itself, denotes traits related to the female sex and is already widespread in the creative and cultural industries. Furthermore, the notion of femininity is socially constructed - it denotes traits that are associated with persons of the female sex, but do not necessarily have to be associated exclusively with it. In this paper, we have opted for film as a sub-segment of the creative and cultural industries, upon which we will exemplify differences and similarities in the display of femininity. Considering the choice of directors, Pedro Almodovar as a Spanish director and Woody Allen as a Hollywood director. Each of them understands and portrays the notion of woman and femininity in their way, and they are perfect examples for a great comparison. In this paper, we will also touch upon the differences between the concepts of gender and sex, gender and sex constructed reality, femininity and masculinity, types of women in film and the film work in general and both of directors way of work. We will analyse six films from 1988 to 1999. When it comes to Pedro Almodovar's films, we opted for: "Women on the verge of a nervous breakdown", "High Heels" and "All About My Mother". On the other hand, when it comes to director Woody Allen, we opted for: "Another Woman", "Husbands and Wives" and "Mighty Aphrodite". Given that the films are from the same period and the leads are female, it will be a perfect example for analysing the theme of femininity in film as a sub-segment of the creative and cultural industries.