These excerpts are taken from letters written by Philip Dormer Stanhope, Earl of Chesterfield, to his son. Originally collected and published in 1774, ‘Letters to His Son on the Art of Becoming a Man of the World and a Gentleman’ was a widely read etiquette manual and precursor of today’s self-help genre.

Bath, October 12, 1748

GOOD COMPANY (AS I have before observed) is composed of a great variety of fashionable people, whose characters and morals are very different, though their manners are pretty much the same. When a young man, new in the world, first gets into that company, he very rightly determines to conform to, and imitate it. But then he too often, and fatally, mistakes the objects of his imitation. He has often heard that absurd term of genteel and fashionable vices. He there sees some people who shine, and who in general are admired and esteemed; and observes that these people are whoremasters, drunkards, or gamesters, upon which he adopts their vices, mistaking their defects for their perfections, and thinking that they owe their fashions and their luster to those genteel vices.

… Imitate then, with discernment and judgment, the real perfections of the good company into which you may get; copy their politeness, their carriage, their address, and the easy and well-bred turn of their conversation; but remember that, let them shine ever so bright, their vices, if they have any, are so many spots which you would no more imitate, than you would make an artificial wart upon your face, because some very handsome man had the misfortune to have a natural one upon his: but, on the contrary, think how much handsomer he would have been without it.

London, December 30, 1748

Your dress (as insignificant a thing as dress is in itself) is now become an object worthy of some attention; for, I confess, I cannot help forming some opinion of a man’s sense and character from his dress; and I believe most people do as well as myself. Any affectation whatsoever in dress implies, in my mind, a flaw in the understanding. Most of our young fellows here display some character or other by their dress; some affect the tremendous, and wear a great and fiercely cocked hat, an enormous sword, a short waistcoat and a black cravat; these I should be almost tempted to swear the peace against, in my own defense, if I were not convinced that they are but meek asses in lions’ skins. Others go in brown frocks, leather breeches, great oaken cudgels in their hands, their hats uncocked, and their hair unpowdered; and imitate grooms, stage-coachmen, and country bumpkins so well in their outsides, that I do not make the least doubt of their resembling them equally in their insides. A man of sense carefully avoids any particular character in his dress; he is accurately clean for his own sake; but all the rest is for other people’s. He dresses as well, and in the same manner, as the people of sense and fashion of the place where he is. If he dresses better, as he thinks, that is, more than they, he is a fop; if he dresses worse, he is unpardonably negligent. But, of the two, I would rather have a young fellow too much than too little dressed; the excess on that side will wear off, with a little age and reflection; but if he is negligent at twenty, he will be a sloven at forty, and stink at fifty years old. Dress yourself fine, where others are fine; and plain where others are plain; but take care always that your clothes are well made, and fit you, for otherwise they will give you a very awkward air. When you are once well dressed for the day think no more of it afterward; and, without any stiffness for fear of discomposing that dress, let all your motions be as easy and natural as if you had no clothes on at all. So much for dress, which I maintain to be a thing of consequence in the polite world.

London, September 22, 1749

I am very glad that you have received the diamond buckles safe; all I desire in return for them is, that they may be buckled even upon your feet, and that your stockings may not hide them. I should be sorry that you were an egregious fop; but, I protest, that of the two, I would rather have you a fop than a sloven. I think negligence in my own dress, even at my age, when certainly I expect no advantages from my dress, would be indecent with regard to others. I have done with fine clothes; but I will have my plain clothes fit me, and made like other people’s: In the evenings, I recommend to you the company of women of fashion, who have a right to attention and will be paid it. Their company will smooth your manners, and give you a habit of attention and respect, of which you will find the advantage among men.

London, January 25, 1750

In every language, pray attend carefully to the choice of your words, and to the turn of your expression. Indeed, it is a point of very great consequence. To be heard with success, you must be heard with pleasure: words are the dress of thoughts; which should no more be presented in rags, tatters, and dirt, than your person should. By the way, do you mind your person and your dress sufficiently? Do you take great care of your teeth? Pray have them put in order by the best operator at Rome. Are you belaced, bepowdered, and befeathered, as other young fellows are, and should be?

Greenwich, July 8, 1751

To neglect your dress, is an affront to all the women you keep company with; as it implies that you do not think them worth that attention which everybody else doth; they mind dress, and you will never please them if you neglect yours; and if you do not please the women, you will not please half the men you otherwise might. It is the women who put a young fellow in fashion even with the men. A young fellow ought to have a certain fund of coquetry; which should make him try all the means of pleasing, as much as any coquette in Europe can do…

I cannot conclude this letter without returning again to the showish, the ornamental, the shining parts of your character; which, if you neglect, upon my word you will render the solid ones absolutely useless; nay, such is the present turn of the world, that some valuable qualities are even ridiculous, if not accompanied by the genteeler accomplishments. Plainness, simplicity, and quakerism, either in dress or manners, will by no means do; they must both be laced and embroidered; speaking, or writing sense, without elegance and turn, will be very little persuasive; and the best figure in the world, without air and address, will be very ineffectual. Some pedants may have told you that sound sense and learning stand in, need of no ornaments; and, to support that assertion, elegantly quote the vulgar proverb, that GOOD WINE NEEDS NO BUSH; but surely the little experience you have already had of the world must have convinced you that the contrary of that assertion is true. All those accomplishments are now in your power; think of them, and of them only.

London, November 20, 1753

Whether, where you are now, or ever may be hereafter, you speak French, German, or English most, I earnestly recommend to you a particular attention to the propriety and elegance of your style; employ the best words you can find in the language, avoid cacophony, and make your periods as harmonious as you can. I need not, I am sure, tell you what you must often have felt, how much the elegance of diction adorns the best thoughts, and palliates the worst.

I repeat it to you again, for at least the thousandth time, exert your whole attention now in acquiring the ornamental parts of character. People know very little of the world, and talk nonsense, when they talk of plainness and solidity unadorned: they will do in nothing; mankind has been long out of a state of nature, and the golden age of native simplicity will never return. Whether for the better or the worse, no matter; but we are refined; and plain manners, plain dress, and plain diction, would as little do in life, as acorns, herbage, and the water of the neighbouring spring, would do at table. Some people are just come, who interrupt me in the middle of my sermon; so good-night.

Philip Dormer Stanhope, Earl of Chesterfield, lived from 1694 to 1773.