The dress shirt is probably the closest to the body so pretty much, I say never.
I don’t like the look. I’ve seen some guys try to pull it off but really a shirt breast pocket? I don’t even like making shirts with breast pockets. I usually recommend men not to have it. And even if you buy something off-the-rack, a lot of times, you can remove the pocket as well.
There are many reasons to have a pocket.
I’ve got a good friend in sales and he’s always moving and he keeps pens in it. In fact, the shirts I make for him have special pockets on the inside for holding his pens. He doesn’t really use ones that leak ink, so I don’t think he’s ever actually lost a shirt, to those of you that object to that.
But if you use it, go for it but don’t stuff it with a pocket square.
My answer is you can wear a pocket square with a vest sometimes.
No – If you’re wearing the vest under a jacket.
Yes – If you’re wearing the vest by itself.
I’ve seen the latter being done by a lot of men.
I’ve got a good friend who’s a photographer. He’s at weddings all the time so he wants to have his arms free because he’s moving and he uses the pockets to actually hold pieces of gear but still he wants to look good.
I think he wears a bow tie with the pocket square and it looks good. It shows that he went the extra mile but at the same time, he’s at work so he follows the function path.
I always believe function first, style second. So in that case, it looks great.
I think a jacket should always have a pocket square.
I know it takes a while for guys to get used to it. I have a client over in Dubai named Sandiv. He talked about how he just left the other day and forgot his pocket square.
He actually stopped at a store to buy one because he felt incomplete without it. When you can get to that feeling, it’s a great place because people notice these pocket squares.
Start off small.
Start off with white.
We look at pictures of Harry Truman. He was a haberdasher before he became president of the United States.
The guy knew how to dress and he looked good. He always had that little square fold there.
4. Overcoats (Trench coats and any type of jacket)
Here is where function happens. An overcoat is there to protect you when it’s cold outside. No need for a pocket square there.
Most likely you’re wearing a jacket underneath and that’s where you would have the pocket square.
You may say, “Well, why does it have a breast pocket?”
That’s where you could possibly put your gloves or to put sunglasses or something in that pocket. It’s not really so much for adornment. That one is more for function.
And there you have it.
I talked about the four points:
- Dress shirts – Never.
- Vests – Sometimes especially if you’re wearing it by itself.
- Jackets – Always.
- Overcoats – Rarely.