(A few years late, but) My favourite travelling hats are these squashy hats that roll up into a supplied bag, with a sprung coil around the edge, made of suede, leather, kangaroo or canvas, by Barmah of Australia.
I think this UK distributor has a better website than the manufacturer. Prices are something like £33 (canvas), £40-50 (leather), £65 (kangaroo).
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Yes, they have a bit of the “Crocodile Dundee” about them, but it’s an authentic look.
Apparently I have the “1025 Suede Hickory”. It has been used in the Outback, during Indian monsoons, up mountains and volcanoes, and picked up some wear but I think it’s only looking better with age.
If price is no object, then you really need to look at Tilley Hats.
They are basically an institution amongst those that own them, and have definitely been designed with at least most of your criteria in mind.
I don’t own one, and am not enough of a hat person to be able to bring myself to spend ~US$80 on one, but having met people who have owned them I can definitely see the fascination with them – especially when it comes to travel. Google will find you countless reviews, and you’ll have to look hard for one that isn’t favorable.
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