So, I am popping in out of nowhere, but I had a sudden flash of insight about hairstylists when I saw your post and read your concerns. First, you are absolutely lovely in all of your photos. Any suggestions about your hair are entirely about how you can bring back that feeling of joy and freshness and fun to your hair, not, absolutely not, about fixing a problem. There is no problem here. Your hair is very nice. That doesn't mean you aren't entitled to switch it up and have a little fun, though.
Here's my insight: Think of your cut and your stylists the same way that you think about wardrobe classics. As Angie often reminds us here, classics do not exist in a vacuum. Classics have high longevity, but they need periodic updates so that they look current. Your stylist may be a rut caused either by how he cuts hair (does he continue to take new classes to update his skills?) or about how he thinks about you! It sounds like has a rigid idea of what your hair options are. He is thinking, "A, B or C works for her" and he isn't thinking maybe A with a bit of G thrown in would be fun. He is thinking about all the things that haven't worked for you in the past--things that may work for you now because your perspective has changed.
So your old stylist is cutting your hair in an unchanging classic way. You are feeling like that classic needs the little tweaks that update it so that it continues to be a modern classic. A new stylist isn't weighed down with the knowledge of the things you've tried in the past. It might be very worthwhile to try a change! I wouldn't make a huge change right out of the blocks, though. First, I'd have any new stylist cut your hair in its current style, but with any updates that he or she thinks are needed to make sure it is current and flattering. That may do the trick!
