I don't wear mine often enough to get a sense for how they break in -- I do feel that they're fairly stiff leather, and using a leather conditioner might be a good idea if you want them to soften up.

For all their stiffness, they haven't rubbed any blisters on me, which is more than I can say for some canvas skimmers I've had, so I've been pretty satisfied.

And, yay, kittyshoes!