I carry a 35liter bag which holds the bulk of my stuff. It sometimes gets checked, but depending on the airline I can sometimes bring it as a carry on. I've used a 55liter bag before and would say that's perfectly fine to use, just don't expect to use it as a carryon. After that I have a sling bag. It's really a cheap fanny pack that I carry over my shoulder. It's enough space for my phone, wallet, passport, phone charger, hand sanitizer, etc. All this stuff could fit in my pockets, but it's more comfortable and convenient to carry it in a sling. It's also safer since I can wear it over my chest to keep an eye on my objects. This is what I mostly use for the plane and for walking around a new city. It's also no problem walking around with my big bag and my sling at the same time The Third bag I carry is a folding backpack. Something like this. It folds down and is kept in the bottom of my big bag. I use it for days when I might need to carry something more. A towel for a beach day, picnic lunch for a day hike, souvineers I plan to get somewhere, groceries, laundry, etc. One other thing I could suggest, see if your smaller bag fits into your larger bag. I use to do this when I carried a big single compartment backpack. I had a second smaller backpack inside it that I could take out and use when I got to my destination. It make sorting my things when packing a lot easier. I've switched to a better big pack pack with more bells and whistles, so I don't need to do this anymore. But it's an option to consider
