So I'm going to offer a somewhat contrarian take for this sub. I too found myself attempting to optimize and reviewing premium bags for this exact purpose. When you really think about it, an under seat personal item, with your main bag in the bins above you, is a pretty limited use case. Do I really need to spend $80+ for something so specialized? I arrived at, "No". Two bags that I have come to love that are reasonably affordable: 1.) Bellroy City Tote ($$) --> Limited organization, but folds down super small and has nice long handles for a tote, which makes it easier to carry with a backpack 2.) Draw Blank Canvas Crossbody Tote ($) --> Only $9 on Amazon. I like this bag because it can be either a shoulder tote or a crossbody bag. It also has a zipper to keep everything contained. Minimal to no internal organization, but you can definitely throw pouches in there. It rolls up well and is very compact as an additional bag.
