don't worry about if your pocket square drops a bit in your pocket, don't aim to look like a perfectly staged and photographed menswear blogger all day long. Clothing should come alive when you wear it, it moves with you, it wrinkles, pants get frumpy, jacket elbows wrinkle and you should be as physically and mentally comfortable in a suit as your are in jeans and a tee.
Your post was epic, but to me this is the most important part. When people are starting into the coat and tie world, menswear blog photos are very misleading. Those have been carefully studied and everything has been set up to look neat and tidy, but as you very well have pointed out, clothes just can't stay like that for the whole day. I remember I was rather worried about linen wrinkling, shoes creasing, tie knot becoming messy, etc. when I started dressing "better". But sooner or later you stop thinking about such things. During the day, flannel pants are going to become a mess, like it or not. Your pocket square is going to do funny things, your shirt is going to wrinkle, your jacket is not going to look perfect when you are sitting or moving, and your shoes are bound to have permanent creases after a few wears. If you don't learn to live with it you're going to be fussing with your clothes constantly, and you're going to be (and look) uncomfortable.
It's OK to make things look tidy before you leave the house, or for everyday's WAYWRN pic if you like, but then you have to forget about what you're wearing.
Edited by RDiaz - 3/1/13 at 12:34pm