I never considered something like that, but I suppose my first two thoughts would be, how heavy is it, and how would it be secured to the bike? And then how secure is the bike?
I have been happy with my setup which is a backpack that I rack (except for my road bike, when I wear it). When I go in a store, or in to lunch I wear the backpack. It can be a little bulky in the winter, but, really not that bad.
But, now I'm curious, like you to see what others have done with lockable trunks on their bikes.