Used to have long hair that I pulled back in a ponytail for cycling.
But it's so straight and flat, that it always looked icky.
So I chopped it all off and go short now. I don't have the hair-sticking through the helmet issue, b/c I usually use a headsweat or buff, but then, that creates problems of its own. Short hair looks gross after a sweaty ride under a buff - and I'm not talented or creative enough to do anything with my buff other than wear it over my head, hanging down in the back. Nothing fancy with it.
Can't win. Levi L. has got it right.....