I don't have much room to talk as I'm not SLY yet either but I agree with everone else here. You are a natural for the 'sly look', You'd carry it off really well.
No doubt many of the guys on here will tell me to follow my own advice but if I were you I would not hesitate. I can however understand the wife/family related concerns but I'm sure your wife would get used to it and end up loving it.
In my opinion there are two kinds of cool looking bald guys. The first are obviously those with the shaved 'sly look'. Then there are those like myself, who probably better suit a tight buzz or all over stubble. You definately belong in the first category.
So good luck and go for it!
Rob