Mine were pretty comfortable from the start - that's one of the main reasons why I bought them.

For reference, I have the Ohana's which are rubbery. I can't speak to their leather ones which might be different.

For comparison though, I had the rainbow sandals with the leather bottoms and those definitely felt very woody, and even after a year I didn't feel like they got any better. Maybe with more time they would have improved but the sole started to split about a year in, so I never got to find out.