I love your question, Bijou. I think at the end of the day I always have some HEWI as a kind of unfulfilled longing or Holy Grail. Once I find it, I all of a sudden obsess over a new one.
Until recently it was nude booties with a pointy toe and low, pointy heel, but comfortable. I found them a month or so ago: Impo Navika booties (see Find 1 below).
Now I am obsessing like an unrequited lover over a burgundy velvet dress. It has to be fitted on top, preferably a wrap; it has to have a swishy skirt (i.e. not pencil or straight); it has to have long sleeves; and preferably the sleeves must have some kind of interesting detail or shape. The ones I did find aren't working (one is out on my size; the other doesn't fit me well; see Finds 2 and 3 below).
PS. JAileen, I recently got Impo Norris tall boots in navy (see Find 4 below) and they are amazing. The navy color is lighter in person than online, and they are comfortable and warm.