The motif of portraiture in art has been present since the earliest beginnings of human interest in fine arts. Portraits have historically served as a kind of document through which a person with all his characteristics was depicted. Portraits were used to pay tribute to loved ones and loved ones. We can still see this psychological characteristic of portraits today in children who, in their first depictions of a person, always depict a person close to them, most often a parent or other family member. Looking at children's artworks, we often see very similar depictions of a person, which vary depending on the stage in which the child is. Among other things, this paper explores how directed observation affects the representation of a child's portrait, as opposed to a portrait without directed observation. In older children, depictions of a human will differ in depictions of details and gender. This paper presents the developmental phases of artistic creativity in children and their characteristics related to the depiction of the human figure and face in artworks. Also, the paper shows works with motifs of portraits of selected artists: Henri Matisse, Oscar Kokoschka, Pablo Picasso, whose works served as an incentive for children's artworks. In the second part of the paper, art activities and works of children are presented, similarities and differences of individual works are compared, and a review of directed observation in the works is presented. Through detailed methodical procedures, the ways in which the children tried to depict the portrait and place it in the period characteristic of the artist whose works served as an incentive were shown.