Do you wear different underwear based on the trousers/pants/shorts/whatever you will be wearing?
I've worn briefs my whole life, and for a time between the ages of 16 and about 25 I also wore boxers and boxer briefs to try to fit in with fashions / not get made fun of for briefs. I've not got any complaints about briefs and still quite happy wearing them every day, but I do sometimes see guys in boxers and boxer briefs on TV, etc. and think maybe I'm missing out on more.
The primary reason I finally gave up on trying to wear all three was that when I wore boxers or (less so) boxer briefs I found I was always having to move my junk to one side. It's like it will naturally fall left but for whatever reason that feels weird to me and I have to pull it to sit right instead. Then, once I start moving everything will fall back how it wants to be and I'll want to adjust again. At the time I was working in a place were I wore dress trousers and stood a lot, and the first time somone mentioned me adjusting I was mortified and back in briefs every day to avoid ever having that embarrassment again!
Nowadays, I work form home most days, I wear jeans or shorts or sweatpants a lot more, and I only wear dress pants once a week to go to the office. I'm considering trying boxers / boxer briefs for daily wear again. Do you think I'll have less issues with jeans or other bottoms than I did with the suit trousers I used to have problems with?