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I think I have seen @pdlouche show some messenger bag he had made, maybe worth asking for the custom route rather to make compromises on "generic" bags?
Does anyone know of a messenger style bag that has that hoop thingie on the back so that you can slide it onto the handle of your wheelie luggage?
There are plenty of bags with that slide down possibility, but I have only found designs with handles and a a zip on the top like a lady's handbag, as opposed to shoulder strap and front flap like a classic messenger.