The study investigates the relationship between people’s personality and the types of hats they like and would be willing to wear. The question is of interest for the psychology of personality and aesthetic preferences, empirical aesthetics, and potentially also for marketing studies. 539 Italian adults completed an on-line questionnaire showing black and white images of 34 iconic types of hat (set 1) and 8 types of baseball caps (set 2) one at a time. For each hat, they were asked to rate how much they liked it and how likely it was that they would wear it.