Dress For 55 Degree Weather. Plus its seam-free so it. But in the winter id probably be wearing jeans and a long sleeved shirt.
For this consider wearing a blouse or shirt with jeans or capris. Jeans leggings or anything that covers your entire legs. If you want to wear a skirt then you definitely should wear leggings too.
Stocking caps for colder weather and stationary or light exercise.
When it comes to outfits for 50 degree weather most people think you HAVE to wear boots just to stay warm. But thats not always the case especially if the rest of your attire is lined up to keep you feeling toasty warm. I know what youre thinking vests are pointless they dont keep you warm etc. Keep a jacket handy in case the date goes on all night.