It is tough to make the decision to go sly to begin with but once you take the first step and get a proper buzz cut to start you will wonder what all the fuss was about. Once you have had your head buzzed for a while it is only one more step to becoming a cool, sly guy. My advice is next time your haircut is due go to a real barber and ask for a military buzz cut & enjoy the "trip", mate.All the best.(P.s: looking at your photo, you would definitely suit a short buzz-cut & shaved head.)
There's obviously a reason, a feeling that you are increasingly become aware of. If you want to stay true to yourself, it cannot be ignored. Sly is waiting but you don't have to leap, just take the first step. To begin turn that fear into excitement. Have trust in that feeling, go the buzz cut, take that step