I say go for it. Few things look worse than a guy who should have given it up some years ago, (nothing personal, just my .02). Not quite there yet myself, but when the time comes, off it comes.
The hurdle to be overcome is the perception of ourselves to which we are attached. Problem is nobody else has that image. They see what is visible, like a comb over, for example.
Maybe this could be an opportunity for reinvention of your look. Time and genetics conspire against many of us. Better to be a self-confident bald dude than a schmuck with a comb over, (my .02 again). Good luck, let us know how it goes. I'm betting the chicks will dig it. Speaking of which, any female feedback on the topic?