The way children portray emotions in their drawings of human and nonhuman topics is assumed to reflect their artistic, emotional, and cognitive development. This study was designed to investigate the development of expressive drawings during childhood and into adolescence, using a large age range (5–15 years) and sample size ( N = 480 ), so as to provide a precise and comprehensive view of age-related changes in children’s ability to produce expressive drawings. More specifically, we focused on children’s developing ability to use the techniques of literal and metaphorical expression, either alone or in combination. We also examined the effects of sex, topics (house, tree, or person), and the depicted emotion (happiness or sadness) on the use of each expressive technique. The main findings were that there is a developmental shift between childhood (5–10 years) and adolescence (11–15 years) in the use of expressive techniques, from simple (literal) to more complex forms of expression (metaphorical).