As long as he has pants on, I don't see why not. Also, as long as he isn't playing with himself or showing himself off to other kiddos, it should be fine. I suggest you don't let him get into the habit of not wearing underpants though.
Normal underwear. Men's or women's depending on who is playing
Of course it is. In fact, a 14 year old should wear underwear or panties. They support the rear and also shape them up so they do not become rather, well, saggy. So, yes, it is very much okay for a 14 year old to wear underwear or panties.
Underwear from the Gods
The best way to wear underwear for 5 days is to wash it. Underwear was invented so you can wear your larger, outer clothes for five days, while you only need to wash your small underwear every day or two.
Wear underwear fit to your body or not bunched in any areas. You don't need to get a wedgie while running or working out! All you need are regular underwear.
subject to opinion but why sacrifice one shred of your dignity voluntarily
none he doesn't wear underwear!!!!!!!!!!! none he doesn't wear underwear!!!!!!!!!!!
It has been scientifically proven that underwear are beneficial to people who have to sneeze while they have diarrhea.
Underwear?
Yes, matadores wear underwear.
Yes. You should wear underwear!!
the Romans did not wear underwear but they may wear a bit of leather