An interesting question was asked of Rav Yuval Cherlo, regarding boys wearing earrings. Some people have responded to the discussion with criticism of Rav Cherlo, saying things like he shouldn't be involved in this, why not discuss allowing makeup, etc. I disagree - guys have been wearing earrings for a long time, and I find it interesting that someone asked if it is ok.

The question posed was by a father saying his 15 year old son wants to wear an earring. They are a religious family and he will allow it only if there is a clear hetter for it in halacha. He repeats that he wants the answer to be clear and not disputable.

Rav Cherlo answered that:
1. It is difficult today to see an earring as specifically female, especially when it is worn in only one ear.

2.  There is opposition in halacha to some modes of dress, due to the issue of non-Jewish culture. While difficult to say it is clearly prohibited for this reason, if his purpose in wearing it is as an expression of distancing oneself from Judaism, then it is prohibited.

3. from an educational perspective, the parents should challenge their son. Since it is not clearly prohibited, but it might be wrong for cultural reasons, yet it is difficult to force a 15 year old boy to do things against his will, this is what should be done: Allow the boy to wear the earring, but because it might be an expression of rebellion, despite the boy's denial of any such intention, explain to the boy that the allowance and permission is dependent on going through a strengthening process in spiritual matters at the same time, with him choosing the path. This way, it wont be against halacha, and will prevent the earring from turning into a symbol of rebellion. Rather, it will even be the stimulus for spiritual inspiration.