I've gone from romping around in summer dresses to needing about five layers just to step a toe outside in a matter of a handful of weeks. It seems almost cruel. I have the obligatory few weeks of scrambling around trying to adjust every single year, and during that phase I usually keep within my little sartorial safety zone.
This usually consists of varying numbers of thermal base layers, and an experiment in knitwear along with a refamiliarisation with my scarf collection. Black Milk sure does brighten things up on these occasions, though.