I thought I’d join in the bag fun.
My EDC (now used for hauling things out to the patio when it’s warm enough for the home office to move there) is Timbuk2’s Classic Messenger, the small size. (I picked it up on a great sale last fall. I had a previous version of their classic messenger that I still use as a backup/extra. It’s lasted for years and is still usable, but it was bigger than I needed now that I carry less than I used to, and it was showing some wear and tear.)
Here’s what it looks like from the outside:
Under that flap are some nice additional pockets: a slash pocket, a zippered pocket that has a lanyard and clip for a set of keys, and an additional zippered pocket that’s accessible even when the top flap is closed and buckled:
The inside is remarkably roomy:
It holds a 13” MacBook Pro (2019) and 11” iPad Pro (2018) with the Magic Keyboard. On either end are a pair of computer glasses (I wear no-line bifocals, but they’re not good for screen distance — gotta love middle age!) and a pocket umbrella. The inside zippered pocket holds various small items: Kleenex, lotion, hand sanitizer, gum, and the chest strap that came with the bag (which I never use, but this was as good a place as any to keep it).
The smaller pockets (which are hard to see here) on the outside of the zippered pocket hold business cards, a microfiber cloth, pens, and AirPods Pro.
The fuschia item in the main compartment is a small packing cube with an interior mesh pocket. It holds an Anker battery, iPad charger, MacBook Pro charger, and various cables for charging on the go.
During the first half of the semester, when I actually got to teach in person, I could fit my lunch in there, too.