Lord Chesterfield is best-remembered for his witty and wise epistolary legacy, collected in Lord Chesterfield’s Letters (public library; public domain). The letters, penned mostly to his son and godson, cover everything from politics to literature to love and offer an ever-entertaining blend of timeless wisdom, practical tips, and very questionable moral advice. But if there is one thing for which Chesterfield remains particularly known, it is his exceptional sensitivity to societal customs and his finesse in gracefully navigating them for his benefit.

In this letter to his son from November of 1745, for instance, Lord Chesterfield captures in one short passage the essence of fashion, the enormity of its enduring allure as a form of social currency, and why it mesmerizes us so:

Do everything you do well. There is no one thing so trifling, but which (if it is to be done at all) ought to be done well. … For instance, dress is a very foolish thing; and yet it is a very foolish thing for a man not to be well dressed, according to his rank and way of life; and it is so far from being a disparagement to any man’s understanding, that it is rather a proof of it, to be as well dressed as those whom he lives with: the difference in this case, between a man of sense and a fop, is, that the fop values himself upon his dress; and the man of sense laughs at it, at the same time that he knows he must not neglect it. There are a thousand foolish customs of this kind, which not being criminal must be complied with, and even cheerfully, by men of sense. Diogenes the Cynic was a wise man for despising them; but a fool for showing it. Be wiser than other people, if you can; but do not tell them so.

Complement with this vintage guide to do’s and don’ts in the art of conversation and history’s finest fatherly advice, including Einstein on the secret to learning anything, John Steinbeck on falling in love, and Sherwood Anderson on the creative life.