I didn't think the leather was stiff, but it is thick and the quilting gives it a lot of "body", so it has a nice sturdiness that I like.
It is a good size bag - you could definitely carry your stuff for all day in there. I had originally thought of getting this bag, with the idea of using it as an evening bag:
But I just like the larger size better, more fits, and the option of using the top handles or the chain handle is nice. Also, I think the large bag is more of a statement, more modern looking, while still maintaining that nice vintage-y vibe that I like.