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
