Much of what a man considers appropriate or pleasant to wear is dependent on his circumstances and taste. But there are still rules or guidelines that can govern what he should wear. The key is to formulate a rule that includes the individual’s taste and circumstances into the equation – as a variable that is different for each man, if you will.
The best such rule is: A man should be as formal as the occasion requires, and as dandified as it allows.
This is a simple rule but more useful than one might think. It urges you to first consider what formality your day requires, and therefore ensures you never look out of place or overdressed. And then it suggests you consider what dandification (read flamboyance, peculiarities, sartorial quirks) it can bear, ensuring you are never bored by your outfit nor miss an opportunity to experiment.
It also, perhaps obviously, varies for any man in any context. If you feel that your age, seniority in the workplace or reputation affect how much dandification your day allows, this will become part of the equation.
Dandification itself is best considered to revere tradition, yet contain a persistent air of risk. To quote Nicholas Antongiavanni: “While often unusual, the dandified always follows the classic rules of dress, or else is based on a judicious breaking of those rules. It is never costume – not spats and ascots, but waistcoats and handkerchiefs. Yet there is always some risk in wearing what is dandified, unless you have so much reputation that a certain eccentricity, even extravagance, is taken to be your due.”
So how much risk does the occasion allow? That is another way to read the second half of this rule.
Another observation on dandification worth making is that, unlike formality, it is not reinforced by the presence of similar items. While there is some balance to be achieved in having, say, a slightly unusual belt in order to draw attention from rather unique shoes, most of the time striking garments achieve their greatest effect in subdued surroundings.
As hinted at in a previous posting on this site, Jeeves and Bertie Wooster are a good model for this formal/dandified balance. While much of what Bertie favours is over the top, you wouldn’t want to look like Jeeves all the time if you could help it. Despite Jeeves obviously being constrained by the proper uniform of a valet (a gentleman’s gentleman, as Jeeves would say), it seems unlikely that he breaks out in yellow checks and bright knitted ties when off duty.
“Therefore, a man cannot follow the predilections of Jeeves, lest he end up looking like an undertaker, nor can he in all things imitate Wooster without coming off like a riverboat gambler” (Antongiavanni). The same rule, in different words.