There are very few occasions in modern life in which most people make an exception to the normal super casual, relaxed life style of modern men. Going out to eat, even at expensive, deluxe restaurants, is no longer much of an occasion. No one dresses up for the theatre any longer, or, for that matter, to go to church. But there are still a few times when men must dress and act as if the occasion was “special”: weddings, funerals, any religious observance, around those who are very ill or dying, when hoping to have sex with someone for the first time, or any other time of profound significance in terms of life changes or events.
In the modern world, a sign of worldliness is to treat any occasion as if one has “been there, done that”. One would not wish to be exposed to ridicule by acknowledging a sense of awe, or that one is witnessing, or experiencing, something that is rare, or delicate, or just very important. But a gentleman is not concerned with the appearance of experience; others may judge as they wish, but he knows that he is a man of the world, and yet wishes to see things in all their wonder when possible.
He is, however, concerned with making sure that a special event remains special for those who attend, and that profound events are given their due and respect. As usual, his concern is with the feelings of others, rather than enhancing his own status. At a funeral, he does not laugh, or tell small jokes; there are times for laughing and joking, but a funeral is not one of them. He dresses in dark clothing to indicate that he acknowledges the feelings of regret and sadness by those closest to the dead; he does not himself pretend more sadness than he actually feels, but he acknowledges the sadness of others in a quiet, gentle way.
At any special occasion, the object is not to draw attention to oneself, but to pay attention to those for whom the day is most important. There is an old joke about the man who “had to be the bride at every wedding, the corpse at every funeral.” Make sure people aren’t telling that joke about you by deferring to: the bride and groom and close family at weddings, those likely to be most aggrieved at funerals, the comfort of the very ill or dying when you are in their company, the feelings of true believers in any religious ceremony, and the parents on the occasion of a new life entering the world.
At all such occasions, acknowledge the expense and trouble that your hosts have gone to by dressing in whatever fashion your hosts deem most appropriate. For most weddings and funerals, a nice dark suit and white shirt is fine. A special occasion means that special attention, some special thought, should go to your attire. Jeans and a tee shirt almost never qualify. The question is not what you would be most comfortable in, but what would make your hosts and other guests most comfortable, and acknowledge to them the importance of whatever occasion is being celebrated. Sometimes being a gentleman means just fading into the background.