The automatic response when one man asks another what color socks he should wear is that they should be similar to his trousers, so as to provide an uninterrupted visual line to his shoes. But rules are made to be toyed with, and one way to demonstrate a proper dégagé, or casual, air when circumstances call for it is to wear hose that relate to little or nothing else in the ensemble, like our man in the Esquire illustration.
Of course, the thing behind all this is that well dressed men are supposed to carefully plan the day's clothes so that it looks as though no thought went into the combination, and that the happy result is mere chance. This is not easy stuff. I for one instinctively reach for things that match too much of the time, but I've found that the simplest way to look properly careless is to make certain that my pocket squares and my socks look as though they were chosen at random.
Wearing socks that relate to nothing else on one's body that day opens a variety of possibilities. On the most pin striped of days a bold man can still don a pair of wine colored hose. And the sky's the limit the rest of the time. Orange with red dots anyone?