What a great pinboard, Anna. I picked up this leather vest on sale but haven't worn it for lack of ideas - some good ones on your board.
I see your style shifting too, but not exactly in the structural way of interesting shoes, topper, done. It may be that all your pieces are so interesting and cool. That is, I don't see you having anything generic that you dress up with a topper and shoes around the edges. Or to put it another way, simplifying the way you put your outfits together may not produce a simple look.
Although, I do feel your latest outfits have been less ornate (?) in effect. Actually what I feel is you've gone from "Russian ballroom at night with a million candles" to "up the whole night at Scandinavian midsommer."
I really love it. But I don't know what you have in mind. If you want to take it further, how much further, etc. Anyways to actually give my answer to the question: I'd give myself a good year to take a style change to completion. Maybe two even.