I'm 54. I've been going to the same hair dresser for 23 years. I have let my hair grow out by a lot. I walked in and her first reaction was to not recognise me. I asked if we could talk privately before she started. We went into the back room and I told her I was transitioning.
She didn't know anything about the process of transitioning nor any other transgender people/clients. But her first reaction was to say oh my god you look like you need a hug, come here. She was fantastic.
She is all excited about transforming my hair from guy to girl over a year. I wonder when she will start charging me from column B?
If you are in Chicago, I strongly recommend her. She spent a bunch of time showing me how to care for longer hair. I was clueless. It's a heck of a lot more work to prepare to walk out of the house, even in guy mode.