Why do some men (boys) wear earrings?

To rebel. Many men wear earrings to show that they are non-conformist. In our society it is becoming more and more difficult to separate yourself from the masses - to be an individualist. I think earrings and tattoos fall into the same category. People want to be different - to stand out from the crowd. But the more people that adopt a fad, the less the more the actually conform. In the end, I think the best way to stand out is to simply be your own unique self. But a lot of people have trouble just being themselves. They are afraid to be totally transparent, therefore they resort to other means to try to stand out.

Many men also wear earrings to rebel or stand out in the crowd. People like to do things which they are instructed not to do. Many also tend to think that wearing it would separate themselves from the masses
- to be an individualist.
The truth is as much as you want to be in the humans who wear earrings category the truth is you're not. You're in the males who wear earrings category. This is slightly abnormal in our society, it won't hold you back at work as much as wearing high heels would, but it won't help. This is unavoidable because people make subtle judgments of everyone they meet constantly and it's mostly unconscious. It'd be nice if no one was discriminated for having bad taste in fashion or something like that at work but it's unavoidable. Feminism is able to tackle the issue of gender discrimination because it is such a wide sweeping issue that we can work hard to retrain people. But you can't retrain people to not discriminate at all. People need to know that the guy coming out of that dark alley with his hand in his coat probably isn't going to be your friend, and those sorts of judgments will inevitably continue into the rest of your life. Basically unless Donald Trump starts wearing earrings you're screwed. The image out there is that being an earring wearing male is unprofessional and that judgment would be nearly impossible to change. This is true in the same way a guy not wearing suit is considered unprofessional, or a guy wearing an 80's sport jacket. People need ways to try and figure out who cares more about the job and while they aren't always accurate, it's not changing. Its' pretty clear to me that men and earrings are going to have a tougher time advancing in corporate America. Just don't do it.