Always. Don't own any underwear.
🙌🏽👍🏽The hallmark of a true man!

(Incidentally, neither do I, my partner/best friend, nor most of our friends**) 😉
**and those few that still own some - and god knows why - never wear it either.
 
Also sometimes. If I keep only the cock loose, it won't swing as much if the balls are not swinging and hitting it along throwing it back to the other side, whilst they're kept in a holed up boxer. It's the first layer of showing less bulge when I'm walking around. It's quite effective, but in very hot days, it's unpleasant.