I'm 42.

I wear my hair longish, several inches past shoulders. for riding I wear is pulled into a ponytail with a soft scrunchy and pulled through the opening between the helmet tightening lock and the helmet. No damage from the helmet.

For endurance activities (very long rides) and triathlons, I braid it, otherwise it becomes a big dreadlock.

I would wear my hair longer if not for trimming off the damage from swimming/chlorine/sun/highlighting.

I used to wear my hair short (pre-fitness) and don't really like short hair on my anymore.....I associate it with my non-fitness lifestyle.