I realize this topic has been dead for a while; but I figured I'd give my input to it =)
To be honest, my choice to shave my head was entirely impetuous - a decision made out of frustration during a period of depression.
To provide a quick backstory: I'd gotten tired of constantly trying to hide my receding hairline (NW3) under a hat. It's really frustrating being 22, in college, surrounded by NW0/1s everywhere, and watching your forehead seemingly get bigger every day. I'd managed to hide my receding hairline for years with really long hair in a "swept" haircut, but in another moment of depression (it has not been a good year) I decided to cut it short (why? I needed change). When I cut it short, I had that terrifying realization that "oh no, I can no longer hide this."
Anyways, that led to my eventual shavedown back in August.
My initial reaction was excitement at the change. No longer did I have to worry about people judging my receding hairline!!
But then came my self-confidence issues. I'm very pale, have a pretty big head, am fairly skinny (though I work out a lot, I can never put on much mass because of my metabolism) and have the largest Occipital Bun I've ever seen (complimented by an odd neck structure I've always had that curves along the back, giving me a fairly "gollum" type look from the profile). All of these factors converged, and I started wearing the hat every day again (still do, though I also still shave every day or two).
I dislike the idea of people seeing/judging me from the side. I know that it's irrational, and completely routed in my own issues in self-consciousness; but I think it comes with my past of having been bullied/emotionally abused.
Maybe someday I'll be more into the sly look; but as of right now I wish I had my long hair back. Even if I used it to hide, I had much more confidence back then.
I included a pair of pictures for reference haha.
Thanks for reading! Sorry it wasn't the most uplifting story; but hopefully things will improve.
Long hair
Sly