I hope that these thoughts have helped you, TG. They were very interesting to read.
FWIW, I think you can have a set of style descriptors that convey your style authentically all year round - and for a while. Modern, Simple, Clean, Bold and Dressy has worked well for me for three years and I see no need to change them unless they begin to feel off somehow. Having these adjectives in the back of my head as a frame of reference, has REALLY helped me focus when I purchase and put together my outfits. So personally, I've has success with the strategy. (High five, Astrid).
I echo what Janet said by a billion percent. For some, the analysis is fun up to a point. For others, the analysis is as fun as sporting their sense of style. People are different, and as long as we keep on having fun with fashion and style, finding the strategy that works for you is key. Setting yourself free after some restrictions makes is a great way of putting it.
Becoming more self-aware in all aspects of life is a beautiful thing - it benefits you and those you engage with. The older I get, the more self-aware I want to become. (I SHUDDER at how un-self-aware I was even as recently as back in my 30's). This is a journey that is interwoven with your personal style. The two feed off each other, which is why style is from the inside out.
So TG, that's my long ramble. But in short, you are on a deep journey to self-awareness in all aspects of your life - and it's a GREAT journey. xo