You do it or you don’t. Is the way I’ve always viewed shirt monograms. But when you do it, there is only one way to do it. Discreetly.
Historically, shirt monograms were used to identify a man’s shirt when it was out for laundry. Courtesy of modern efficiency and organization, there is no longer such necessity. But has that fact barred men from monogramming their shirts? No, it has not, nor should it. Nowadays a shirt monogram is something a man should wear for himself, not for those around him.
So, if you are a monogram type of guy there are three decisions you need to make: placement, font and color.
There are numerous acceptable placements for a monogram. Instead of listing each location I think the best guideline to observe is that the monogram not be visible when a man is wearing his jacket. Many men praise placing the monogram below the left rib cage, fine by me (see 2nd photo, white shirt from Knot Standard). However, I favor placing my monograms on the sleeve placket (3rd photo, blue houndstooth shirt from CottonWork). In this location the monogram is completely out of site when wearing a jacket and when not wearing a jacket it is still mostly out of site (for me it is still out of sight as I pretty much always roll my sleeve up when not wearing a jacket). I believe I remember Old Man Will remark that he likes his monograms on the inside of his collar, another good place. The place to not put your monogram is on the edge of the shirt cuff (1st picture, blue oxford). I played around with this placement on a few shirts and could not get over the ever-presence of it, even when in a matching color to the shirt. Never again. I still cringe when I see men with monograms on their shirt cuffs that are of some contrasting color in script, that is the worst case scenario. If you have any of those shirts, use them for rags.
There is only one acceptable font for a shirt monogram, block font (if you really must then some type of arial or times font). I have mixed, but mostly negative, feelings about the diamond monograms (where the surname initial is in the middle and of a larger font size), so I prefer to steer clear of those. I mention this style in particular because I think it is the second most common, after block font. So let’s say that any form of script or design brings more attention to the monogram if it is spotted, which is antithetical to the point of monogramming your shirt. It also just looks foolish. So let’s just not do that.
When something is hidden from plain view does it really matter what color it is? Yes and no. I think navy and black are the two most common colors for shirt monograms. But I have seen them in pretty much every color there is. I personally prefer to keep them the same color as the dominant color on the shirt (all three shirts). This helps maintain that whole concept of being discreet.
Whether to monogram or not is your prerogative. Just remember; placement, font and color. In that order.