In London I pretty much lived in some variation of the same outfit everyday. Sweater, fur gilet, coat, jeans and ankle boots. It kept me warm, but not overheated, whatever we were doing. I especially loved the days when I had to pull out the sunglasses - because that meant the sun was out!
The only error I made was choosing fashion over comfort (and failing to pack anything in the way of a comfortable alternative). While my boots are exceptionally comfortable running errands in New York, I will say that by day three of walking all day, my feet were feeling a little worse for wear. Maybe some more practical shoes next time!