Been having trouble this spring with boxers. Never did before. I do a lot of hiking and I've gotten badly chaffed on the ball sack. I started using talc powder as a dry lubricant and carry a tiny bottle now in my pack. That seems to help but still, what a pain. A raw open wound on the balls when you are several miles in the woods is not fine.
Looks like boxers just aren't practical for athletic type pastimes. I wear bike shorts when cycling , maybe I'll try those instead while hiking. Or just go back to using jockey shorts. I'm hesitant to free ball for the same reason.
I assume you mean wearing boxers under long pants? In which case I'm not surprised you got chafed.
Best hiking wear, in my opinion, is COTTON briefs - not synthetic - not overtight, but firm enough to hold everything in place. Over those: if it's warmish weather, shorts - fairly short but not too tight, so you get a bit of ventialation. If it's too cold for shorts, then long pants. I probably wouldn't recommend my supertight jeans for long walks,
but I don't think it's necessary to go to the other extreme with really baggy pants.
Chafing is caused by two things: rubbing, and sweat. If you sweat a lot it might be worth changing your underpants halfway through the walk. The tal
powder is a good idea, though it's only a preventative measure, it won't help much if you have already got chafing. Vaseline can help too - and of course Vaseline is useful for other things....:blushing: