Going sly early isn't what it used to be. Even a decade ago if a young kid was shaved/bald he was automatically a skinhead/gang member or some kind of indie/punk wannabe. Now people of all ages go sly and it doesn't have the same stigma. People (especially dudes) will give you sh*t for it but deep down they're scared because they know one day they'll have to face it. As I told my friends when they ribbed me about losing my hair so young (I'm 19, started balding probably 2 years ago), I'd rather deal with hair loss at 19 when everything else is going great in my life than stack it on top of a heap of problems when I'm 40 or 50 (not to say that life is shitty at that age but I'm enjoying having basically no responsibilities!).
I know a lot of guys are worried about what girls will think but the most successful pickup artist of our generation is Neil Strauss and he is proudly sly.