I have a bag with a shoulder strap that I take in addition to the small (pull along type) bag that I put overhead. The bag with shoulder strap is kind of what you might see guys taking to gym. It is small enough to go on the floor under set in front of me. I shove my small purse in this bag to consolidate bags when going through security. With taking your shoes off, etc., it's a pain keeping track of everything.
I learned a long time ago when my luggage did not make it to my destination, to carry toiletries, meds, & clean underwear in a bag that does not leave my hands.