"All mankind is running to monograms this year," wrote the New York Times Style section in June, 1902 (click for the fin-de-si‚àö¬Æcle puff piece.) Apparently, monograms were the pants or ties of the age. Since then, what originated with the crests of kings became a not-so-subtle talisman of status more than style, practical in white-collar and dry-cleaning Post-War days and was eventually almost extinguished by the rise of the logo. Granted, monograms have been mostly the provenance of oil-executives since the Patrick Bateman era, but that's no reason not to dapple in initialization.
Now, we agree with the venerable Style Guythat monograms can appear ostentatious. But, as a nod to past styles over current ego, use them as a rare chance to play with an old art. If you stick to small, traditional contrast-stitch initials on the upper right of your pocket pleat on your favorite brand shirt as offered by Harrods, Bergdorf Goodman and other respected sources, the monogram becomes a quiet surprise beside the lapel. Embroidery on the button pleat of your lower shirt tail is also acceptable if hidden by the waistline (forget the sleeve.) And no cuteness with your chosen letters and stick to sans-serif fonts unless you really latch into a cursive or more formal design that remains subtle.
Certainly, the boarding-school pedigree of the three-letter mark plays well with the current fad for everything preppy and beyond (see Obedient Sons, Thom Browne or RL's Rugby) as monograms are another aspect of the current yen for old codes and rules. Generally, stick with what the shirt maker offers—most high-end lines sold through your better department stores will have a trusted partnership on the ground to do the work for you. If you do strike out on your own by contracting embroidery or designing a monogram yourself, we suggest you trust the intuitions and opinions of your tailor before your own—they get paid for this, you know. The Times of 1902 also advised relying on expert advice, "It is lucky, take it as whole, for there is sure to be no color profanity in the result, as there might be if the non-professional set about making combinations." Yeah, that.