Troy Patterson hazards an answer:
A conspicuous monogram is classy only in the sense of business-classy, bespeaking time lost loitering at the SkyMall which invites the striver opportunities to attach his initials to golf bags and playing cards and coolers that convert into portable stools. The people most likely to be impressed by the embroidery are by definition allergic to the ideas that elegance is restraint and discretion the better part of not looking goofy.
Ultimately, unless you’re headed to summer camp (in which case your belongings might get mixed up with others’) and/or you have a “Memento”-like case of amnesia, it’s probably best to avoid the monogram:
”[You’ll] want to know that some of your superiors believe it correct to monogram only linen and silverware—and that your superiors include people of the servant class. One never tires of quoting the words of Stephen Fry’s Jeeves to Hugh Laurie’s Wooster, on the subject of a monogrammed handkerchief: It was the valets understanding that this sort of thing was “only for those people who were in danger of forgetting their names, sir.”