As a follow up to my last posting, here are some tips on stuffing a handkerchief.
The golden rule: a silk handkerchief should always look as though it is in use, though this is patently not the case. It should be casual, and not appear overprepared or constructed. If you are lucky this may counterbalance the fact that you are wearing one. And no one else is.
The easiest way to achieve this casualness is to hold the handkerchief in the centre, let the four ends drop, and stuff that centre into the bottom of the pocket, letting the points poke out of the top. If the points poke out further than desired, try folding over the other end an inch or two first.
If you prefer a rounded finish to a handkerchief (and it does look rather less outspoken) then reverse the process. Gather the four corners together, perhaps fold them over an inch or two as above, and then stuff into the pocket so the centre protrudes. This may also be useful if you wish to display the centre pattern, rather than a differently coloured border.
The other alternative is a mixture of these two, gathering the four corners and then folding the length in half. That way both the centre and the corners protrude, with the centre acting effectively as a fifth point. The disadvantage of this stuff is that there is no handkerchief at the bottom of the pocket and, unless the pocket is tight, it may slip down during the day.
I would also recommend trying a no-nonsense stuff, particularly if you feel the other suggestions don’t work. Push the handkerchief into the pocket. If the protrusion at the top is too large, fold the excess silk back into the pocket and behind the handkerchief. This rarely results in the same display twice.
Finally, the second golden rule: always go for casual. Don’t over-think it and, whatever you do, don’t adjust it constantly. There’s nothing worse that someone fiddling with a pocket hankie, drawing more attention to an already unusual decoration. Clothes should look, to quote Hardy Amies, as if you had forgotten all about them.
Cotton handkerchiefs are different. Some of these pointers apply, others don’t; more on the folding options for a cotton handkerchief at another time. As to which you should wear, though, bear in mind that a silk tie or handkerchief works well because of its contrast in texture, between the rough wool of a suit and the smoothness of silk. Silk therefore goes best with most suits, particularly flannel. Some modern worsted suits reverse this relationship: they are so smooth that cotton or even wool is more of a contrast.
(Remember the philosophy of Permanent Style though: you don’t need to follow the guidelines, it’s just worth being aware of why they are there. If you wear a wool tie or handkerchief with a sports jacket it might get lost because of the lack of contrast. A silk tie with a shiny suit might be too much. But then you might want that.)