Thank you so much everybody! This is helpful. The skirt stays. I will post updates.

I think you have it sorted out.
In your wardrobe do you keep things that are not in the style groove you aspire to? I know I do, some days its just gotta be artistic although that is not at all what my wardrobe is like. Other days it is just melt into the background where I tend to wear things that aren't quite me probably because I'm not quite me that day...

Freckles, yes, i'm like you. I think these "melt in the background" pieces are essentials, although I wouldn't count them in my wardrobe per say. I view them more like my gym clothe or my winter gear: necessary, but not style defining. (Although I am coquette with gym clothes, yet not enough to start doing a huge overhaul).
Some days, I won't want to be badass just like some days, I don't was to be "pretty".