Either banjo logo is great, either the very first one or the latest, but I favor the half-guitar. Understated and classy.
Cotton, definitely. Pockets at least as an option, not only for glasses, but a pen and a notebook. (Never know where you're going to find new lyrics.)
Please, PLEASE, no political statements! How many times do I have to plead with you, dammit, leave us fascists alone. You, too, may be elderly and Republican someday, if you learn to read and the neighbors let you live to grow up. (Kidding, just kidding.)