The ones mentioned above are pretty classic looking and formal so I'm not too worried about them going in and out. I guess it depends on the style/colour/material. These are more for work / smart occasions.
I definitely agree! I have recently bought a couple of nice handkerchiefs and like the "puff" style for when I'm out of a night. For work I usually dont bother though. I've been tempted with some of duchamps handkerchiefs of late, they are pretty interesting.

