Watching with interest as I’ve never found the right one for me, don’t drive so use it for commuting and general shopping etc. I’ve had:
2001 Patagonia Critical Mass. Still got it but it was never great, just a big floppy messenger. Worked well for lugging boxes on my bike as it sort of just wrapped round them. My Mrs still uses it as a weekend bag.
2004-2008, Crumpler something. Fabric was rough, pretty indestructible but didn’t get on with it. Then some North Face thing, that was rubbish.
2008 Osprey Flap Jack. OK as a slightly nicer laptop bag but not great for cycling. Sat in my office now, as a slightly nicer laptop bag for walking to on-site meetings.
2010ish medium Timbuk2. probably the best messenger I’ve had for cycling, but the strap annoys me. think they’ve changed to seatbelt material. Still looks mint, should’ve got a bigger one.
Current bag is an Osprey Momentum 32 backpack. Somehow manages to be massive on my back but tiny inside. Pretty hard wearing and has a waterproof cover, but low level annoying.
I’ve looked at Life Behind Bars bags but feels a bit risky buying one without seeing them. Not sure I’d want to pay Mission Workshop money. Bagaboo look good, especially with the extra cross strap.