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· Honors Member and King Fop
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Over obsessing over a pocket square is not really part of the Ivy tradition. A white linen PS goes well with everything except a white linen suit. Add a pale blue linen/cotton and a paisley silk print and you should be set for life.

Now if we really want to get into the weeds of this subject, I've heard of 2 theories of PS selection. The operative word is they are just THEORIES.
  1. Coordinate color and pattern of the PS with those of the shirt. They should not match exactly but rather complement each other.
  2. Contrast the materials of the tie and PS. e.g. if the tie is shiny silk, the PS should be matte linen or wool; and vice versa
But really, it's your wardrobe and your ensemble. I feel you'd almost have to go out of your way to pick a pocket square that absolutely clashes with the rest and therefore is 100% wrong.
Wool pocket squares are something of a rarity in my experience. In years of haunting men's stores and departments, the only ones I have seen were at Bloomingdale's a year or so ago. I bought a couple, and just by chance I happen to be wearing one at the moment. The vast majority of my squares are silk, distantly followed by cotton and linen.
 

· Honors Member and King Fop
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6,034 Posts
Quality-wise, a $150 square from Brioni does not differ from a Jos Bank square, which can often be had for $10 or less. Both hand-rolled printed silk; the JAB might be bigger actually.
So it has always seemed to me. In fact, squares are about the only thing I buy regularly for myself at JAB. I was just wearing one today to a most charming high school production of "Anything Goes." I think I was the only man there wearing a necktie, to say nothing of a square.
 
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