Don’t buy the ones from Classic Parts as they are hollow rivets that fit sloppy and don’t seem like they will hold up over time. Having a lathe, I reused the nylon rollers, remade the rivets solid and peened them over. Turned out well.
The ones I bought from The Filling Station had solid rivets just like the originals.
I think the nylon roller would be the way to go over leather. But if you want to try them, soak them in water (or maybe oil) to make them pliable. I don't think they're going to be that durable.