The Challenge:Jumper Dress from Delia's $39.50
The Additions:Striped Polo from Abercrombie and Fitch. $39.50Black Cardigan from Old Navy. $34.50 Free People tights. $28 Delia's Black Ballet Flats. On sale for $24.
This is enough layers for the fall where I live, but probably not the rest of the US. Add a plaid/tweed jacket for extra warmth.