I'll just recount a little story from a Christmas party I attended last year. Most of the men were very well dressed, but hardly any of them rocked the square. I commended one little fellow for sporting a square. He replied, "MEN don't wear pocket squares, GENTLEMEN do!" The "little fellow" turned out to be a retired jockey (our host is a very prominent turfman) so obviously a tougher, braver man than I ever was!

Unless I am wearing a "beater" sport coat for yard work or walking the dog, I invariably wear a pocket square in a jacket that has a pocket for one.

"Ascots and pocket squares,
that's what every cool guy wears!"

I tend to feel that if you want to look dressed up and you can be bothered to fold up a handkerchief/square and stick it in your jacket pocket quite nicely, why the hell not just wear a tie. They're both just superfluous bits of cloth that don't actually perform any function.

I don't really have an issue with it as something everyone does. First of all because I don't that's true where I am, so I don't have the same perspective on it that Beeston does. In the 1950s or 1960s many men wore them, not as an affectation but as an automatic part of wearing a suit, and if someone wears them the same way today I have an issue with it. I also don't have an issue with a pocket square worn a la Prince Charles - it's obviously a conscious choice, not simply automatic, but he uses his squares to add something to the outfit, as they usually are a different pattern than his tie and rarely plain white.

But I do have an issue with it:

a) as some kind of standard of "good dress," as if you're doing it wrong if you don't wear one. "An outfit isn't complete without one," or some dreck like that.
b) as pure affectation. There was a hilariously overblown discussion of pocket squares a while ago in this Styleforum trad thread I keep an eye on (we all need a laugh now and than) that really summed that up. Minute discussions of the pros and cons, with this jacket or that tie, etc. Someone even wrote "especially if you’re going for the Trad’s nonchalance it can really make you look like you agonized over it." Aren't you agonizing over it right now? How can you "go for" nonchalance? Unreal.

I just don't wear them because I don't care. I don't own any, don't want to spend the money on them, and don't think they'd look good on me if I did. But I'm not against them on principle.

It was hard enough for me to learn to tie a tie with these big roast beef mitts of mine. I don't need to be fussing with yet another piece of cloth....

Here's my "thought" process, if anything so muddled can be described as such:

Working day, sport jacket, no tie, chinos, rumpled Irish poet look. Carrying a notebook, camera, 87 pens and hand computer. And reading glasses.

This last item is the key. I need to get at the cheaters, and the handiest place by far to stash them is jacket breast pocket. Square gets in the way.

Or:

Highbrow concert of group my elderly mother sings in. No honorable way to get out of it. Thus, jacket, wool pants, tie, pocket square, good shoes (as opposed to mocs or Bean boots or something). It's appropriate and I don't need my cheaters to sit in the back and look at the ensemble. (And looking at the program just makes it go on longer.)

And I won't be overdressed. If anything, I will be the master of subtle elegance, with the rumpled Irish poet lurking just below the surface.

There is nothing wrong with a handkerchief. OR a large rose gold watch with complications. OR fancy socks. OR double monks. OR that contrast lined jacket. OR....