Years ago, in hippie stage, I grew my hair out. I just didn't get it cut for almost two years. It looked like hell.
I've learned since then that you can grow your hair out and still have it look good. The secret, perhaps unfortunately, is to find a good hairdresser. Tell her (or him) what you want it to look like in a year and she will keep trimming it so that it will grow out to that and look good in the meantime. It may take a little longer to get to the style you want (but maybe not) but you won't look like Medusa as it grows.
How do you find a good hairdresser? I'm not sure, but what worked for me was that every time I saw a woman with hair similar to mine (texture, thickness, natural curl) and who looked nice, I would ask where she got it cut. I've been very happy with how that worked out. (BTW I was stiill presenting male at the time.)
Tell your hairdresser the general parameters (shape, length, how much daily effort you're willing to put in) and let her (or him) do their magic.
Good luck!
- Kate