Yeah, guess it is a balance…why we are on this forum. Left to myself, I can get a little quirky. Too much into an aesthetic and not enough reference to environmental norms.
I could do that as a city girl, no one really cares in a city, be an art object if you like.
But in a smaller community, or as part of a business team, It really pays to strongly reference current style, so as not to stand out as weird. I firmly believe the best disguise for actually being weird is looking mainstream current. People’s eyes just glide off you. As opposed to sticking to your outfit and wondering what the heck.
My style icon is Tilda Swinton, which probably tells you I am an art object at heart.

I also lean more in choosing to override trends with my own natural/personal (or aimed for?) aesthetics but would like to do it in a modern/contemporary way (achieved with new fabrics, textures, colors, juxtapositions, etc).
Great thread lots of science and philosophy here, will be a great read for me on the weekend.