Norman Clegg - a Northern English folk hero; from TV sitcom Last of the Summer Wine
Flat cap or beret? For me it is always flat cap, and never a beret.
A flat cap is the English National Costume for men.
I wear a flat cap pretty often, at most times of year. I even have a worsted woollen one for winter that has ear warming flaps that fold down. And a spring/ autumn cap made of corduroy; and for summer a linen one (which I keep in the car, and wear as a sun shade).
(I don't always wear a cap! Since I am bald, I always wear a hat of some kind outdoors - perhaps most often a Tilley wide brimmed thick cotton hat; and in the winter a Tilley thick woollen hat with a moderate brim and concealable warming flaps.)
Because I've been wearing a flat cap since mid teens, I don't feel self-conscious about it. But a beret? Well, that's a different matter altogether. I have never stepped-outside wearing a beret, because I would feel like a fool.
Why should a beret make me so self-conscious? Is is the association with pretentious beatniks? Or is it simply because of the French connection? For the English, the French are the Old Enemy, and are stereotypically wearing a beret (the kind with a little stalk on top) and horizontally striped shirt.
In general, I regard the beret as unpatriotic.
Of course there are British Army units that wear a beret. And General 'Monty' Montgomery sported a particular type that was named after him. But it still fails to convince me. Perhaps beret-wearing was imposed on our army by the Frenchified Norman Upper Classes?...
From a practical perspective; the beret strikes me as merely a dysfunctional flat cap; one that lacks the benefit of a brim. Its only advantage that I can imagine is to be more secure in a strong wind.
But then, in a wind, I do what the Northumbrian shepherds do; and pull my hood up and over the flat cap - to retain the benefit of the brim.
Rationality aside; I can't shake that reflex response that there must be something wrong with anybody who wears a beret, voluntarily and in public. So there it is.