Originally Posted by Holdfast
Until a month or two ago my answer was I would always wear a square with a tailored jacket. But since then I've experimented combining them with jeans and as a result of feedback here and in real life, I've stopped using a square in that context. Just looks better without frankly.
I would now extend that principle to say that anytime I'm wearing particularly casual trousers such as jeans with an odd jacket, my default position will be no square. Smart trouser and jacket, the square's back. And almost certainly if I'm wearing a tie, I would want a square.
I like to wear this one with jeans and an odd jacket:http://www.fourinhand.com/Product.as...uct=FHSQ-Lin16
The texture of the linen and the light blue color complement jeans well IMO.
To answer the title question, I'm new to wearing pocket squares, but I'm now very rarely without one.