I have 2 sons, 8 & 18. When both were little I let their hair grow out. When each was around 3 years old, I gave them the traditional clean-cut boy cut, after that we let it grow again.
Xander hasn’t been around other children much except for one year in Kindergarten. He had longer hair than most and I think everyone was too young to think anything of it. Then in 1st grade, covid was in full force and we went to virtual school. He had a new class with new peers and often was referred to as “she” or “her” and he would say weekly “I am a boy!”. The worst was in IEP meetings and conferences when teachers said it while sitting there with his file.
Society wins.
Xander: Momma you need to cut it ALL OFF! I’m tired of being called a girl!
Me: Xander, if people call you a girl based on the length of your hair, that is a reflection of them, not you.
Xander: *has no idea what I mean
Me: You are Xander Williams. You are a boy. You are smart. You are brave. You are kind. You are my son. I love your long beautiful hair because it shows me that you’re healthy. Some children, very close to us, do not have the ability to grow hair so I look at your hair as a blessing from God. If you want to cut your hair, we can cut your hair. Just know that whatever length your hair is, you are the same person. Your hair does not define who you are. And if the world can’t see that, that is their lesson to learn.
Xander: I love my beautiful hair, but it is time for a change.
Me: I will get the scissors. 
2 months later:
Xander: I want to grow my hair back, I miss it.
Me: I think that is a great idea.
acurbsideprophet 