Hmmm ... let me think. Soft bags, obviously, because you NEVER know how much headspace or other clutter is in the overhead at your seat.
My lightweight [but quite stiff] Nautica backpack with about 376 assorted pockets - or is it 5? One pocket assigned to travel wallet, another to assorted keys and small change [yes, bank coin bags are essential for multi-currency ops], bill-fold and cellphone. Another with cigarettes and matches for that immediate fix after arrival, camera, notebook and pen. Main body contains lightweight outer jacket [Bill Bass?], spare handkerchief and underwear, book[s], rechargeable razor .... and the inevitable collection of electrical chargers.
Shirt with breast pocket to carry passport and b/c.
Comfortable slacks with nothing in the pockets except handkerchief.
Slip-on shoes.
Anything heavy or bulky from DF gets given to "Herself" to go in her big soft carry-on which contains a book and very little else.