Well, being a chap, I find that wearing a hat especially in Winter is essential but very unfashionable in the UK as most men do not, even in cold or rainy weather. My job took me to Poland for three years and most men there wear hats ( and many women wear fur coats) so I have a collection of two fine trilby hats, some beanies, two fedora types, sun hats, peaked caps and even had a real Russian fur hat that I bought having had a spell in Novgorod )at -15C) in the Winter.
I wore the Russian fur hat shopping with my wife in the UK to a supermarket and the remarkable thing is no one comments whatever you wear so I say to all you other Gramps, don't be shy - get a hat or preferable several!