It never gets too terribly cold in FL and as a result, I don't bother to own a lot of winter clothes. Instead, I have layering pieces. One way I use them is by extending the life of my summer dresses by pairing them with a long sleeve tee and leggings. Make sure the print of your dress is not overly Spingy or Summery.
Jacket: Old Navy
The great thing about FL is that it did not take me long to shed the hat, jacket and scarf!