1 Stuff it. Even if you prefer a square top to the handkerchief when it peeps out of your breast pocket, stuff it in. Just fold it into a square and then stuff it in.
Don’t attempt a razor-sharp thin white line – the so-called TV fold. It looks good in Mad Men because everything about them is that sharp and that groomed. Until you have your suits made for you and pressed every morning, and preferably have your own make-up department, stuff your handkerchief. It should look like it’s meant to be used anyway.
2 Assuming you’re not also wearing a tie, think of the colour of your handkerchief in the same way as your tie. The same dark colours and simple patterns worn just as well. It doesn’t have to be bright.
If you are also wearing a tie, the colour of the handkerchief can pick up on a minor colour in the tie, shirt or anything else. Or pick up on nothing, just harmonise with the other colours (in the same way the tie does).
3 The key to stopping the handkerchief falling down inside the pocket is to make sure part of it is touching the bottom of the pocket. Stuff it in until it touches, then pull out what you need. The Lazy Fold is a good way to achieve this.
4 The only real quality consideration in a handkerchief is that the edges should be hand-rolled: turned and secured with broadly spaced stitches. If there is a straight line of thread joining these stitches, that is a machine imitation of a hand roll.
Beyond that, the handkerchief just needs to be big enough. There is little difference in the quality of the silks.
5 Try wool. Or wool/silk mixes. Silk can be too flashy for some, as can white linen. Wool takes the shine off things, like the pattern shown at top (on sale at Drake’s) and can be both more casual and quietly sophisticated. Traditionally goes well with rough country cloths like tweed, but also a nice change of pace with a worsted business suit.