I once read an interview with the woman who was president of Henri Bendel for 29 years and she revealed her shopping strategy: she bought five complete outfits "at the start of each season" (don't know how many times a year that would be, since the fashion world has lots of seasons) that she felt superb in. Complete outfits down to shoes, bags, jewelry, belts, everything. Then she wore them in rotation (with some of her older outfits) -- but always the same way each time. No mixing, matching or remixing.
I remember thinking that was an excellent strategy -- if you could find (or have a stylist find) those initial perfect outfits. Of course this was a woman who had to represent her store, in the business world, at the highest possible level. But it stuck with me as an interesting way of approaching things -- you still get the fun/challenge of putting together an outfit, you just don't have to do it every time you get dressed.