I painted my my own face today (on computer :D). It’s amazing but I never attempted to paint a person wearing a hat. I attempted to draw a dragon wearing a hat (and yes it looked weird) but not a person. I rarely wear hats despite having three fedoras (gifts). This time I painted over a paper texture in my attempts to make it look like a traditional pencil and watercolor sketch and then added a brown monotone. For fun I colored the eyes blue, which is my eye color.