Yes to both. My black plain leather hamilton is getting a little smooshier. It will always have some structure because it is a satchel, but the plain leather breaks in nicely and isn't too stiff.
I am not sure about the embossed. I did see an embossed peanut in the MK store that had beent here a while. It was softer and a little more bendable than the new slate one they had just gotten in.
Are you considering a large N/S or the medium E/W?