I had almost shoulder length hair in college in the 70s, but kept it “respectably” short during my working years. Toward the end I was working for a public agency that had very flexible dress codes and was tolerant of most clothing and hair styles. In fact, during the time I was there, there were a couple of trans women going through their transitions.
So I started letting my hair grow out, and since my 20s it had gotten thinner and more wavy, so it was very challenging to go through the awkward phase before it got long enough to tie into a pony tail. I mostly wore a hat to keep it down as flat as possible, but of course I couldn’t wear the hat at work (office job). I used a little hair spray but not really enough, because I was too worried people would notice the smell on my bus ride into work. So basically I had very messy hair for a couple of years! Fortunately I retired after the first of those years, so during the second year I could use more spray and occasionally use pins to keep it in place behind my ears. All very frustrating, but after a certain point, there’s no way I wanted to cut it off, only to want to start the whole process over again! (I should say that my wife was always fine with my hair, and has been very supportive of my crossdressing.)
I had mixed feelings about finally having my hair long enough for a pony tail. I was so used to seeing myself with hair over my ears and hanging down in the back, that I thought I looked kind of weird with all my hair combed back and out of sight. It looked like I had short hair again, and a friend even thought I’d had it cut when he saw me for the first time with the pony, only from the front!
But the frustrations and challenges paid off big time as it got longer and longer, and now that it’s several inches past my shoulders, I can enjoy the various feminine looks when it’s down (e.g., pig tails, front sections clipped back, pony tail with small wisps hanging down in front of my ears, long curls in front), and just put it into a low pony tail when in drab.
I do admit it’s a pain to take care of, since it turned out that the longer it got, the frizzier it became! I use a few different anti-frizz products, but they never completely tame it. I know, I’m very lucky to still have all my hair, so I can't complain, but it’s definitely thinning more (and my hairline receding) so I’m planning to enjoy it as long as I can. Oh, and also I’ve had it colored, since it would be almost totally gray otherwise, and that adds to the feminine look which I absolutely love! One final note - I think it has stopped growing. I had it trimmed in May and it’s only an inch or so longer than it was then.