The only accepted time is when a person that is not sophisticated and maybe an "oaf" or "unrefined" in appearance are those that are uncultured and clumsy due to not being experienced. If their heart is open and good with intent, and they just lack the confidence that is the only path.
The key thing is the minute one begins to be stupid, closed-minded, shame, and most importantly judgmental.
I agree with you 110%, having "layers" (i.e. sophisticated) is a very cool and good thing one should have. One that follows the path has the one thing that makes a person interesting.