in the event he does try to wear a mask outside of a hospital setting, I predict he will be mocked by multiple conservative talk personalities and quickly backtrack.

Moving to a policy of wearing a mask regularly, would mean dropping the narrative that Covid will disappear and admitting his previous rhetoric and actions on the subject were erroneous. He's incapable of admitting he was wrong. He may try to wear mask without admitting his past action was irresponsible, but I doubt that will go unchallenged. He'll stop wearing a mask, because in his mind, and those of his most ardent supporters, it will make him look weak.