Glad to be of help to anyone. It was interesting reading about the Florida climate and how it's perceived to be cold at what I would say are ideal temperatures. For instance, to day it was 56 deg. when I started my run of 1.5 hr., and about 70 when I ended. I wore only shorts and a short sleeved shirt and it was perfect. But if I were going to run errands, I would wear jeans, long sleeve top, jacket, shoes and socks, and maybe take the jacket off as the day warmed up.
Those items you put on links for, kimber, are nice things. Watch those clearance items as the size availability is really limited. You asked if I would wear a top under that chill factor top, and I have to say, yes or no, depending on the actual temperature.
If it were 40 deg. out, probably not - or just a tank or waist-long sports bra to add a layer around the middle. If colder, probably I would, and maybe a jacket over it if down below 30 or so. If you're running in 50 deg., I would say, try it alone with some light weight tights, gloves, and see what you think. Sometimes clothing choices take practice just like a new route or distance.
You asked what size tights to get. I generally wear a med. or sz. 8 and go for a sz. med. tights, so you would probably be okay in a small. Unless you are rather tall. Some brands may be different. Personally I think Nike runs small, but it might be that the cut is just for flatter (younger?) figures. You're right about sizes, though - ugh.
