Do you wear a Pocket Square and when not to wear one?

Question

P

Answer 1

Fairies in Neverland don't wear pocket squares. 

Answer 2

Pocket squares are mostly a question of fashion, image, etiquette, ranking, "codes", sometimes of activities, professions, events, myths, novels and/or movies, etc.,

(Sean Connery, for instance)

and here's a "guide":

https://parisiangentleman.co.uk/academy/dirnellis-ten-commandments-of-the-pocket-square/