Depends on the season, though one of them is a standard across the board: I have to have comfortable footwear, to keep the feet happy.
Right now, as winter approaches, the second item would have to be something that keeps my bony frame warm, for hanging out in a house we keep at 68 degrees no matter how cold it gets outside– which means it can get a bit chilly around the edges sometimes. This is usually a sherpa lined hoodie of some sort, from now until sometime in April, or at least a base layer over which I add other items.
Functional, hardly ever fashionable.
3 Cents' 