He says don’t worry about clothes? How would you take that?

He is God, and his references to clothes, I think, should typically be understood as references to types of bodies. A new white robe is put on the baptized person, for example, that indicates the Resurrected body to come.

But as full nakedness is clearly used in the Jewish and Christian baptisms, associated with servants and with Jesus himself, a Christian person has every reason to associate being physically unclothed with being spiritual.

I just reflect that Paul circumcises Timothy with an apparent expectation that Timothy will be seen naked. Was this a regular Jewish practice?