After two or three years of major crisis in my life, I decided to let my hair grow in 2006, right after my daughter's wedding. I had no end game in sight, but decided just not to cut it. I started with a fairly short regular man's haircut and it took probably two or two-and-a-half years to get long enough for a decent pony tail. I'd had long hair in the seventies, but had never worn a ponytail. I did get some pushback when I grew it out, but those opinions just didn't matter to me. At the peak, my hair was to my waist but I usually trimmed it to mid shoulder-blade length.
I had a severe case of covid in 2021 that had me in the hospital for 29 days and the stress on my body ended up causing enough hair to fall out that my pony tail was about the diameter of a pencil. My wife cut it to just above my shoulders and I haven't cut it since. What amazes me is that pre covid my hair was fairly straight, but when it grew out, I now have substantial curl. I've worn it down, without the pony tail, to church a half dozen times. What's really funny is that when I've worn it down, in male mode, I got several compliments, but I actually had 2 bald guys or 2 separate occasions tell me that my hair was "glorious". Exact word.
So having it whatever length will have fans and detractors.
I mostly wear a pony tail for practical reasons. I like to pull it back in a clip if i want a more feminine look. I do a bun occasionally but I'm not proficient enough to get the look I'm after and too lazy to try and figure it out. I don't look like a woman ever. i have very strong masculine features although my weak chin is covered by my beard. My preferred look is very much just on the femme side of androgyny and not like a woman. That's like the world's least favorite look, but that's exactly the look I'd be going for. I throttle my desired expression by 80% because my wife is concerned what others think. But, I've been slowly experimenting with what my end point look might be and incorporating small feminine expressions here and there. I'm probably giving way to much for your OP, but there it is...
