I used a schemagh as a scarf/neck gaiter. I'll have to find something better than that -- my neck definitely got cold, and the airflow into the helmet was more than I liked.
The leather jacket, over low-budget thermal underwear top, was great, especially after (at the far end of the trip) I unsnapped the collar and did the full zip up. A little cold air coming in through the sleeves, but nothing major and a change noted below should help with that.
The goatskin motorcycle gloves kept my hands reasonably warm riding out, but when I had to remove them at the halfway point to fill up the gas tank, the hands got cold then stayed cold all the way home. Other than avoiding gloves-off situations, I don't have a solution for that one.
Jeans over low-budget thermal underwear just wasn't enough. Unpleasantly cold. So the next time I ride in sub-40-degree weather I'll be wearing my old merino wool "union suit" instead of the $10 stuff. That should help with the legs, and with the arms versus that aforementioned sleeve airflow. The only alternative I can think of to better under-insulation would be leather pants, and I just don't see myself as a leather pants kind of guy even without looking at prices.
No problems with the feet. Wool socks under insulated suede hiking boots.
Fortunately, there aren't a lot of sub-40-degrees days in Florida. But I do want to get my kit correct for temperatures down to the 20s. Even if I only ride locally (I do want to eventually take long motorcycle trips, probably on a larger bike), my attitude is that the motorcycle is my primary vehicle (the family SUV is for family stuff or for hauling things I can't carry on a motorcycle) and that I need to be able to comfortably take it on the road in any likely weather.
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