I think for me, my style has evolved in that I am more deliberate about what I buy and how I put it together. In the past, I would buy random pieces that I liked to some degree, but I wouldn't always have any idea how to wear it. Now, I buy pieces that I love and give thought to how I wear it. I also, in the past, had tried to move away from black and into bright colors, and that just really didn't work because I really love black! I wear a lot of black, white, and jewel tones.
Probably the best thing that helped me in this respect was a book called "Style Statement" that a friend on another forum recommended. I didn't read the book, but she posted her process through it and I started going through the process based on what she had done. I still haven't finished it but it has helped me think about what things are "me" and why. It doesn't mean I don't try new things, but I can take trends or leave them.
In the past, for a while, I felt like I was "less" if I wasn't jumping on every new trend. There was a board I participated on that seemed to have conflicting messages regarding trends. But now, I know that some things I will try and some things I won't, and if I miss out, no big deal (especially where I live...nobody would know if it was a trend or not...)
I also have transitioned from a larger wardrobe with a lot of orphaned pieces to a smaller wardrobe of pieces I wear a lot in different ways.