In the heat I like to wear capris and a t shirt. I find wearing shorts to be uncomfortable going in and out of ac and also, when walking around in the FL sun all day I prefer to be a bit more covered up. I had a skin cancer removed from my calf a few years ago so now I always look to avoid sun exposure whenever I can. Also, I like to have a few pockets so I can go bag free when I'm not toting my camera bag around and I have a few pairs of capris that have the deep side pockets that button closed - perfect for cc's, my phone, a small tube of sunblock and a lipgloss! At night I like a casual dress or skorts.
This December I'm not sure what to plan for! When we visited once in early March it was cool in the morning and after sundown but hot in the afternoons so I'm expecting something similar to that. If that proves to be true, I'll still wear capris and tshirts but will have a variety of jackets/sweaters to choose from depending on the weather and I'll also bring a pair of jeans and a hat/gloves in case the forecast calls for really low temps.