Headwear crisis

[EducatingArti]

I'm asking for a friend he's not very tech savvy . He needs some headwear that is suitable for a particular set of circumstances. As he is a migrant, he's concerned that he's likely to need to travel back to his place of origin fairly soon, what with new laws being introduced and all that. As things would have it, this will probably coincide with the birth of his first-born (although he's fairly sure the baby isn't his anyway, but that's a whole other story).
Anyway, he needs something practical for travelling but that will also look good for the usual load of visitors that turn up after the birth.
He was going to go with the classic cloth on head held on by a plaited band but is worried he'd have to put up with being called "teatowel head" for ever afterwards. He's also thought about the simple round hat but although he's a fairly modest man, he does worry that this might lead to him being confused with the dregs of society shepherds.
Would he be unreasonable to stay bare headed? He is going a bit grey and has a small bald spot but hopes this might not be noticed in the general rush of things. Photo attached so you can decide what would suit him best.

Yes, dreaming is in the genes Pickle.
I'm not sure about that particular hat Anne. He might get mistaken for someone else. He also wants to know what a sleigh ride is. He does admit it looks quite cosy though.

Knit. He thanks you for your headwear advice That's just the effect he's aiming for and he agrees with you that flashy competitive gift giving is so awkward to deal with. He thinks it's not too likely to be a problem though as they'll be away from home and owing to some rather awkward circumstances and consequentially tricky family dynamics, he doesn't think anyone is going to even acknowledge the birth let alone bring pressies. A lamb would be a lovely thought though if you happened to be in the area and dropped by.