Z is a pretty typical Modern Orthodox teenager in many ways. He goes to a Jewish day school and spends half the day studying Tanach (Bible and the prophets), Gemara and Hebrew. He goes to synagogue on Shabbat and he is a youth group leader. He plays on his school's basketball, soccer and baseball teams. He plays the piano and likes to read novels. He is also lukewarm about wearing a kippah. I totally get it. It's not always comfortable to stick out and look different than everyone else.
The fact that he does not always have a kippah on causes me angst. Part of me feels like when Z is bare headed we are both being judged. I worry that people will think that neither Z nor our family are really Torah observant or that there is something intrinsically wrong with Modern Orthodoxy if their boys can go out with an uncovered head.
As Z has gotten older he has become much better about wearing his kippah in all sorts of situations and can often be found with a baseball cap on, an absolutely an acceptable alternative. The halacha (law) is not that a boy or man should wear a kippah it's that his head should be covered.
For some people the fact that Modern Orthodox boys in the United States don't always have a kippah on their head is evidence of the failures of Modern Orthodoxy. Truthfully I think it's about boys trying to figure out how to balance the world at large and Judaism. After all being Modern Orthodox is really about having one foot in each world and it's not always an easy balance.
I sometimes feel judged by more right-winged Jews. I know I should not care but I know that the fact that there are MO boys who do not always have something on their head is proof for some that there is something lacking in the choices that J and I have made.
In a way not wearing a kippah is a sort of rebelliousness. Interestingly, for the more right wing community rebelliousness in teen-age boys often takes the form of smoking cigarettes. Z recently said "Wouldn't you rather me not always wear a kippah and not smoke?" Of course I feel that way. I am actually that crazy lady on the street that tells teenagers that they look like idiots when they are smoking!(Tonight my kids made me promise never to say that again when I am with them.)
In my ideal world he would always have a kippah on and he would not smoke but in the world of teenage boys I'll take a bare head and a healthy body.