Welcome CobaltBlue,as you can see there is a wealth of information and support here,you are not alone.
Really, what you do with your hair is up to you, but I believe that if you're thinking about going sly then now is the time to do it & not worry too much about what other's say.
When you have your head shaved for the first time you will definitely have doubts as to why you got it shaved, but stick with it and you will get used to it as will others.
Wow cobalt - have you SEEN the amount of wisdom and support that has been posted on here.
Go for it man. we're all behind you 110%. And post a pic soon