The purpose of this naturalistic study was to investigate the effect of booster seat design on the choice of children’s seating positions during naturalistic riding. Data was collected through observations of children during in-vehicle riding by means of a film camera. The children were positioned in high back boosters in the rear seat while a parent drove the car. The study included two different booster designs: one with large head and torso side supports, and one with small head side supports and no torso side supports. Six children between three and six years of age participated in the study. Each child was observed in both boosters. The duration of the seating positions that each child assumed was quantified. The design with large side head supports resulted more often in seating positions without head and shoulder contact with the booster’s back. There was shoulder-to-booster back contact during an average of 45% of riding time in the seat with the large head side supports compared to 75% in the seat with the small head supports. The children in the study were seated with the head in front of the front edge of the head side supports more than half the time, in both boosters. Laterally, the children were almost constantly positioned between the side supports of the booster in both seats. The observed seating positions probably reduce the desired protective effect by the side supports in side impact, and may increase the probability of head impact with the vehicle interior in frontal impact.