This is a great hat! Very well done. I am going to go against the flow and say fatty braid, but that's just my style. Personally I would maybe make a fatty braid, and then give him the choice between the two.
I love this hat! I have been trying to get up the motivation to make my skier hippie friend a hat, and I think definitely helps me want to do something so rad! I love love love the secret pocket... great for secret notes, extra money, or a little lighter... AWESOME JOB!