Assorted thoughts:
I have now learned that there's no such thing as a "work environment." Not an overarching concept.
I think you could rock anything you had a mind to rock. Not sure what to say about wanting substance to be noticed over style. It sounds laudable but fairly un-Rachy. Style is substance! You are quirky and interesting. Why not show it?
That said I have no clue what your environment is like. Are you actually in San Francisco? Berkeley? I don't know.
I have documented my attempt to soften and casualize and "LA-ify" my work wardrobe. Meanwhile attorney DD is discovering that in LA, in some firms, female attorneys are supposed to be a little bit sexy, for instance sizing down in their Theory trousers. Which is completely hilarious and would NEVER fly in the NorCal financial environments I have spent some time in.
So who knows? Do you? Have you tried it? How did you feel?