I tend to go in phases that I sort of rotate.
For example, this summer I was doing a bold eyeshadow color but applied wet as eyeliner, with a specific neutral pink blush, and lip gloss. The color of the eye shadow changed, but I think I wore that basic formula 3 or 4 days a week for a couple weeks in a row at least.
I also really like to wear one color on my lid, blended into my crease, with no eyeliner on my eyes.
I would really love to play with more dimensional looks, like the smokey eyes, colorful smokey eyes especially, but I always feel confused as to what colors will look okay with whatever color outfit I have on. I feel like I try to match it too much sometimes.
I think I have the confidence concerns as well. I will stick with things I know (or at least think I know) look good on me rather than experimenting too much, particularly if I am going out. I think as my skills improve, maybe I will try more. I have started watching YouTube tutorials a lot again and that seems to be helping me get ideas.