Rules

Nicholas Antongiavanni writes the following about how young men should dress:

For it is very ordinary and reasonable that the old should envy the young, to whom it is given to enjoy so many more pleasures, so much more intensely, for so much longer. Truly, we would marvel if they did not envy them. And this envy extends to dress, because old men wish to reserve to themselves the few pleasures which remain to them to enjoy. Thus they get angry when they see young men wearing double-breasted suits and French cuff shirts. It does not seem reasonable to them that young men should enjoy the trappings of eminence before attaining the reality.

He then continues at a later point:

In addition to those modes mentioned above, these especially are to be avoided by the young man: three-piece suits 8especially if the vest is double-breasted), contrast-collar shirts, two-tone or crocodile or anything but solid calf shoes, hats, pocket watches, bow ties, handkerchiefs, bold patterns and bright colors.

But some things are safe ground for young men:

... blazers and khakis, single-breasted suits, plain black shoes, shirts with barrel cuffs and button down collars, striped ties, belts, subtle patterns and somber colors. And if someone should complain that these rules leave him no room within which to make a profession of style but consign him to dreariness, I reply that necessity forces them on him.

Bearing the above in mind and by reflecting against them, I must note that I have scored very badly. Amusingly enough it seems that based on my experiences in Finland, it is the younger folks who tend to be offended by my dress whereas the older people tend to be fairly supportive of proper dress.

But I will concede and leave my elders with the pleasures of wearing hats and pocket watches. As for the other points, everything's fair game...