I hope I don't derail, but only to give you some ideas, but Velorbis sells bikes with the hooks already integrated into the rack and you can use your own bag(especially leather!) with a handle.
http://velorbis.com/velorbis-classic...c/360d-feature (Click on the rear rack part of the image)
I would imagine those hooks won't be good for bumps, but I think you can alleviate that with a bungee or leather straps.
Speaking of leather straps, you can buy some with hardware already attached to it from acorn bags
http://www.acornbags.com/straps.html I would imagine its the same straps they use designed to attach to the bike and support it's weight.
I'm surprised these types of leather/shallaced bags hook mounts and/or leather panniers in similar style to these business bags aren't more popular in the vintage/classic/euro crowd. They look spiffy, I must say!