This is a tip that I have learned by pure experience: Dress the way you like to dress, not your running errands or gym wear, when you go to get your haircut. Why? Because if you are a little edgier they will think you really aren't even if you tell them you are. Hairdressers are typically cautious when you want something new or if they don't really know you.
Since I lost range of motion in my shoulders, along with other stupid issues, I can't blow dry my hair let alone style it. On top of that I have a lot of hair and its thick, even in my 40's it is still really thick. So I went straight on Pixie, I am one of those people that if life is going to change I am going all in but as I said my hair is very thick and I have a lot of it. In order to get that shape and fringe you need to be aggressive and when I walked in wearing a boxy tee and baggy jeans I didn't look like me or represent my personality very well. So I ended up with a helmet on my head, it was heavy and dowdy.
Now off to the second place, I am from Chicago so I almost went back home for it. This time I wore my favorite Rolling Stones tee, skinny jeans, black blazer and gold stillettos. I told them what I was wanting and that I am not one to cry over hair so no fear. I also went to a man, I find it is harder for woman to be that aggressive with my hair. At the end, and there was no length taken off, there was an enormous pile of hair. It was exactly what I wanted. It was fun and edgy nothing like a helmut. I can style it into a faux mohawk when I wear a black sheath dress to give me that rock n roll edge I like.
Additional Tips:
Interview hairdressers if you don't have one you love. It is an important job and it's your hair.
Make sure your hairdresser is passionate about what they do. You want to make sure they are continuing their education because if they aren't they probably have lost their passion.
As judgemental as this may sound it is the truth, I look at their hair and personal style. Let's face it this is a beauty based buisness and it is the person I am trusting with my appearance and how people judge me. I do not look to see if they are beautiful that is irrelevant. I look at their personal style not their weight or perfect features. I look for someone that best represents me and what I like.
Do not bring in a picture of some celebrity you want to look like. That scares most hairdressers because they will not be able to make you look like Jennifer Anniston no matter how good they are how much you pay.
Be honest about how much time you actually want to spend on your hair everyday and what your level of experience is. You can't bring the hairdresser home with you and if you don't have 2 hours to spend styling your hair you may not want to get too complicated
Typically I don't go in with a paticular haircut I want. I go in with a length I am willing to go to and a general idea what I want it to do with it.
No haircut, hairdresser or magical wizzard can change your hair texture so you need to work with the hair your mom and dad gave you. Trust me the right haircut will make you love your hair. So you know a good haircut looks good with little to no effort because it works with your hair.
A good hairstylist will do a consultation before they wash your hair. I tell my hairstylist, Shawn, that I want to keep it short but other then that whatever you think. You wouldn't tell a cardialogist how to perform surgery. He knows hair, he knows what my hair will do and he is up to date and current with all new technigues or what is more current.
Trust your hairdresser and if you don't find one you do.
Above all its just hair it will grow back so take a risk, have fun and try something that takes you a little out of your comfort zone. Afterall thats what hats were made for.
For any of you that live in the area (St Louis) take it from a hair snob from Chicago that has gone to everyone, everywhere with a big city girl trapped in the middle of nowhere mentality Studio 703 is the ONLY place to go. My family goes there as well. Shawn is my go to guy but the rest of my family uses other associates and we have never been unhappy. Shawn is extremely passionate about what he does. Shawn and his buisness partner Dee are on top of continuing education for themselves and their staff. The staff is proffessional and they all love where they work. I have been going there for years and they have retained their staff with little to no turnover.