Gregory Porter wears a hat primarily to cover scars from skin surgery he had over a decade ago. This distinctive hat, which also includes a strap covering his ears and chin, has become his signature look and a kind of "security blanket." He originally started wearing it for comfort and warmth while performing, and it evolved into a part of his identity. Porter has acknowledged that while he isn't always recognized without the hat, he embraces it as a symbol of connection with his fans. He has not disclosed detailed personal reasons beyond mentioning the surgery, preferring to keep some aspects private.