Flat caps of various varieties seem to have different signifiers attached to them, depending on what country one finds themselves in.
In the UK, they seem to be considered as rural attire or perhaps working class urban.
My Chilean ex-step-grandmother once gave me a black cotton flat cap because I'm a musician. She said that if I ever hoped to make it as an artist, I need to start wearing that hat because that's the example set by Pablo Neruda.
In Canada, plenty of people, both young and old wear them. Some as a nod to Irish or English ancestry, others because flatcaps have been adopted as a hipster alternative to the sportiness of baseball hats.
Flatcaps are not traditionally worn with the kilt. There were apparently some members of the British Royal family who favoured them during the Edwardian era (perhaps even into the reign of George VI?). I've also dug up a couple of drawings from that time period and have come to the conclusion that an exception may be made for people to wear flat caps and kilts together on two conditions: they must have epic moustaches and they must be able to present themselves in black and white
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