I have been getting the Instagram posts from Amy Similovic and there seem some interesting concepts.
One is to buy pieces that you like, that fit with your style words rather than outfits. I remember being told when you buy something think about what it goes with and used to know people that bought a whole outfit.
The other idea I liked is to wear what you have by wearing them in unpredictable ways eg your blazer to the supermarket or cowboy jacket to exercise class by wearing them in different/ unpredictable ways. I guess it takes a lot of confidence.