Here in the South our weather has been a little tumultuous. It is mid November and we have had 75 and 40 DEGREE TEMPERATURES in the same week. No wonder we have a hard time dressing appropriately!
I don't know how you feel about bare legs in cooler temps, but I am game for them if it is above 50. After living in New England for a few years I think I have thicker skin, and then there is the fact that if I wear tights my cats think attacking my legs is a new kind of game. I justified the bare legs with these completely impractical but fantastic flannel booties. Now, I was an amazon woman in 5" heels and could only totter around for a little bit, but man these are amazing and my feet were warm.
I bought this sweater out in Portland and immediately fell for its bold graphic print ( FOUND HERE ) It also reminds me of what I imagine Palm Beach was like in the 70s, so thank you Tory Burch! The skirt is a year round go to for me, because it is lined cotton. I also have a habit of buying in the same color family so I can pair items throughout the seasons. This weather is just plain tricky to dress for, SO IF THERE ARE any RULEs, I SAY just WEAR WHAT YOU LOVE!