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That's true. If you're carrying it by the handle and the buckles aren't fastened, the flap will pull up and back while the bag won't hang straight down.
The strap is single ply leather.
Not to jump in, but the bag hangs correctly regardless of whether you've buckled the flap or not. The handle's only really useful if you've buckled the flap but I find that in cases where I'm rushing out the door it's not too much to put it over my shoulder, throw in my book or whatever's missing, and then buckle it as I walk. The construction is such that it's not really intended as a briefcase (the strap is not removable), it's just a nice convenience to have a handle available. If you want a briefcase, get one. If you want a messenger, get this. You won't be disappointed.
Uh. What.