In short; BootedBear has said it all.   Always remember; it's only hair; it'll grow back. 

I think your face and head shape (from what I can see of it) would take the sly look very well.  I recommend going down gradual;  #3 buzz;  then 2 ..... .     I would bet you like it better and better the shorter and shorter you go.

For myself; I thought I'd never get over my fear of what other people think.  But what I found is that they barely notice it ! ...   Going sly the first time was a BIG BIG deal for me ; so full of fear.   but now;; after a year; i've found that when i let it grow a bit;  (just lately it grew for about 20 days);  and then shave it; I don't feel self conscious at all; i feel like I have come back to "normal" ...   so; it takes some getting used to ; but once you are sly; you will love the look on yourself.  Just take the plunge; (but with 'baby steps')  ... (  i guess that's a contradiction . . . ) ....

Best,
John

Welcome!  Try buzzing it down now and then if you don't like it you can always grow it back out some and have a shorter styled look or a buzz cut of some length - it'll be grown back out enough by January that no one would even know you buzzed it... or after you buzz it shave it slick a couple of times and see if you like that.  What's important is your own comfort level with your look.