The article is about the life and artworks of an Italian renaissance female painter, Sofonisba Anguissola. Its objective is to compare her self-portraits in three different layers- the first one concentrates on formal matters such as composition, colours and theme, the second layer steps out from the frame of the painting and delves into cultural aspects of her life and tries to understand her works in that context. And the third, final layer tries to reveal her own motivations and dreams and looks at her, an artist from those times, through the eyes of a modern woman who, even though living almost 500 years later, thanks to impermanence of art can still feel and experience similar emotions. By analysing her self-portraits, it is possible to see different stages of her life: youth, adulthood and elderly years. Each portrait corresponds to a different type of sensibility, aspirations and desires: from passionate young artist nearly stepping into her professional life, through matured and self-assured woman, till an old matron fulfilled by her life and expecting the end with peace. This great painter not only laid out the style of female portraits for the next hundreds of years but also left us with something like a portrait- journal which can lead to transcendental and timeless perspective into art.