Two experiments examined the development of flexibility of categorization in children aged from 3 to 5, using a picture-matching task. During a pre-test, spontaneous matches were observed. Children were next presented with a scene aimed at inducing an alternative match. Finally, they were given a post-test identical to the pre-test to assess whether they would maintain their initial choice. Both experiments showed that preschoolers were able to produce different types of categorization choices. In Experiment 1, children had to choose between a thematic and a taxonomic option. Five-year-olds; showed flexibility and changed their mode of response more often in the presence of the scenes (experimental group) than in their absence (control group). In contrast, 3-year-olds' responses seemed to reflect spontaneous variability since their switches were not related to contextual information. In Experiment 2, two more choice options were added. Three-year-olds' data replicated the findings of Experiment 1. However, a majority of 4-year-olds were consistent on the thematic mode of response and adapted their responses to the scenes only to a limited extent. Overall, the data suggest a developmental path from spontaneous variability to flexibility, via a predominance of one mode of response.