Great story rbb about your transition and what you went through in your mind as well - thanks for sharing this! I do agree with you that how we wear our hair is just as much a factor in whether it looks old or not. As far as being "a certain age" I think a lot of this also depends on the condition of someone's skin as far as how it corresponds to the hair or not. So, with coloring or not, pay attention to skin care, ladies!
Obviously, if someone is very wrinkly and VERY uneven in tone, the colored hair is going to look odd and especially if it's way too dark. A word about coloring - it seems that so many dedicated non-colorers of hair have this stereotype of the older person always coloring their hair black. Indeed some do, but far from all. With the increased variation in hair colors and products, there's no need to have that harsh look if one chooses to color, or continue coloring their hair. There's any variety of beautiful shades out there, and no, one doesn't have to go in the opposite direction and go "generic blonde" either. The only ones who pull this last off are the ones who had lighter hair to begin with, usually no darker than lightest brown, and they have the skin tone to go with it too. The rest of us don't, especially those of us who had really dark hair to begin with. In our case, going no lighter than a medium shade works better whether that shade have red, gold, ash or neutral tones in it. This tends to go better with the medium complexions than blonde would.
But back to grey - it really does have to be well-cared for, and cut well, whatever length, otherwise it just looks scraggly, and that last indeed does make a mature woman look older than she needs to. We have enough going on with age without making it look WORSE LOL!
All I know, at this stage in the game anyway, I get a TON of compliments on my hair coloring, even from my hair cutter who would be more than happy to tell one if something wasn't working. But I look younger in general and my skin, while not flawless, is still tight and healthy-looking, not much in the way of wrinkling save for forehead wrinkles that have been there for a LONG time. Bangs takes care of that LOL. No Botox or surgery for me, along with jeep here. I'll catch up with her eventually with the grey hair part, just not yet.