Ha Ha, Hi Mike
Listen, that hat defies explanation even in real life. I've never received a satisfactory explanation of why we have it. But, I assure you, it exists. Even worse, it cost me more than 70 bucks, so you know it's for real!
The idea here was to do something like a 17th century Dutch "tronie". You know, where they get some girl up in "oriental" garb. I think Rembrandt did some of his self portraits in this fashion. Only in this case I reversed the East/West roles between the clothing and the subject.
The charcoal is OK, but everybody does those painterly "doe-eyed" girlie paintings. I wanted something a bit flintier; something like the look my wife just gave me when she read over my shoulder and saw your comment about the credibility of her hat. Thanks for the help, Mike. I won't have any trouble getting her to give me that look now!