This study explored appropriate pedagogical directions for observational drawing in lower elementary art education through the “My Observation Diary” project, a six-session program designed to suit students’ developmental characteristics. Data from student artworks, interviews, and surveys were analyzed. The results indicated that first graders can focus on basic formative elements such as dots, lines, shapes, and colors, and that selecting materials with rich color and expressive flexibility supports realistic expression. Four key themes emerged: interest in the observed subject, joy of autonomous expression, self-efficacy, and sensory diversity of materials. Students especially showed strong engagement when expressing subjects related to themselves. Based on these findings, the study suggests simplifying formative elements, designing curricula that promote children’s agency, using accessible materials, and selecting familiar observation subjects for effective implementation in classrooms.