Gregory Porter wears his signature hat primarily to cover scars from skin surgery he underwent over a decade ago. He has openly explained that the hat started as a way to conceal these scars and has since become a crucial part of his personal style and stage identity. He even refers to the hat as a "security blanket" and his "jazz hat." The strap that covers his ears and chin, which some mistake for a balaclava, is actually part of the modified hat design, also originally worn for the same reason. Although he acknowledges that his hat generates a lot of recognition, he has expressed that he wishes people would focus more on his music and heart than on the hat itself. Despite some viewers thinking the hat looks unusual or "stupid," for Gregory Porter, it is a meaningful and comforting part of his public persona born out of a personal health circumstance.
