Originally Posted by HyacinthWhat you really need to do is measure everything you plan on carrying, or at least the largest items and then allow 2 more inches "wiggle room" for getting your things in and out of the bag. My guess just for the file folders would be at least 12x9 inches so there's no way you should be considering bags only 10 or 11 inches across, especially since that's maximum width and doesn't take things like short zippers and rounded corners into account. Keep the measurements and a ruler next to your computer, or measure a bag you already have that holds everything you carry.
You really should be looking at messenger-style bags but there weren't many large Classic and vintage ones made.
Yes, I think you're right on all accounts. I was in my local outlet last weekend and their selection of messenger bags left a lot to be desired. Thank you for all of these helpful tips!