Wouldn't a briefcase, or some type of bag that you carry in your hand, work for anything that can't fit in your pockets? There's no need for a shoulder strap.
I carry a lot of books and papers across campus. It's just not as comfortable as a shoulder strap.
This, to me, is seriously jumping the shark. Wear nice clothes that fit well, stand how you want to stand, carry what you want to carry. I gives a damn about thumb placement.
lol That's me everyday, bro. I recently went back to school to pursue my dream career and one class has 9 books. 9 books! It's killin' me.