I pack some of the same clothing that I do for a ski trip. I agree with the layers. I bring a parka too (has that layer for blocking the wind and rain that is so great and a hood), ski mittens, and hat. A locker is really helpful. Dad rents an
ECV and that big basket is helpful too. And although in nice weather I'm a minimalist in what I bring to the parks, for winter for layers, I like a back pack (more places to carry layers that go on and off). I'm all about having what makes me comfortable and changing vs. being too cold or too hot.
I'm a bit of a cold weather weenie. I'm prepared in the morning with rope drop (excited to get going), then it gets nicer, but then when the sun goes down I'm really more into staying inside. I'm not a big fan of night time skiing either. When my kids were younger, I'd stay with them in the parks for the nighttime shows, but with my kiddos grown and uber/lyft so readily available, I go back to the condo (watch movies, play games, make hot chocolate and popcorn, and chill out inside in the evening). Funny how some others in the extended family end up coming with me. None of the others want to be the first to wimp out, but once I do, I usually have a small contingent come along. After eight or nine hours in the park (which is really plenty), a warm cozy condo is heavenly. I'm in my 60s though and not the diehard I once was.
The parks in the 30s in the evening with the wind blowing just feel really cold to me. 32 is the lowest evening temperature when I've been in the parks, and I don't know what the wind chill was, but burr.
I've spent about 15 different Christmases in Orlando, and you never know what you are going to get. For me it's ranged from lows in the low 30s to highs in the mid 80s. Merry Christmas to all and remember that even without ideal weather it's fun to have an adventure away from work with family. Enjoy and stay warm!