The assessment of creativity arouses increasing interest within design community. The literature witnesses efforts to quantitatively measure creativity, although commonly considered intrinsically subjective. Recent experiences show a good degree of convergence between assessments employing more objective metrics and evaluations of creativity made by experts in design and innovation. With the overall goal of determining whether such judgments are reliable and repeatable, the present paper analyzes creativity assessments of commercial products performed by skilled and novice designers in order to highlight further differences due to accumulated experience. The investigation is carried out by means of a suitable questionnaire asking to evaluate the creativity of 10 market successes and 10 commercial flops. The experiment tests also whether commercial results can strongly influence the perception of creativity. The outcomes reveal that experience is supposed to play a not negligible role in evaluating creativity, while the question about the impact of market success requires further investigation.