I can advise against buying a Jeppesen bag. They are well marketed but very poorly supported. I had an Aviator bag that liked to lose the stitching after about 4 months. The rep I spoke to at Jeppesen told me to take it back to "the store" for a replacement, Jeppesen cannot help me. "The store" is a local FBO that bought half a dozen of them over a year ago and can't send it back to Jepp, so I was stuck.
I'm now using a Cencal and love it, much better made and the one problem I've had with it was happily taken care of by Cencal (the fiberboard bottom was bent).
I would suggest getting a bag large enough for all your stuff. I know some pilots who have a small bag overflowing, or just leave stuff at home hoping I bring it
Now I also fly with people who have bags large enough to sleep in...so somewhere in the middle.