I usually wear boxers, sometimes boxer-briefs or nothing.
My cock winds up down one pants leg or the other in most trousers. I tend to get a bit chafed by slacks with a rough crotch seam, so I "shift gear" from time to time so that it is either at 5:30 or 6:30. That tends to equalize the skin irritation and give one side a rest.
I have a couple of tailored suits in which the slacks were cut so that I could consistently "dress left".
In some pants, when going up and down stairs while wearing loose boxers or no underwear, the damn thing spontaneously shifts from one side to the other with each step up or down, which feels rather creepy. Has anyone else experienced this?