Ok: Being from both climates (Orlando and Chicago, but Chicago first), I always ask this to my mom when I travel up north.
It's tough to explain. Since we are a warmer climate down here, 70's/60's can seem chilly to us Floridians. Something like that can actually kill our oranges and plants.
On the same side, a 60s/50s up north can make me freeze while my mom thinks it's warm (yes, it's warmer considering it might have been below zero the day before. Whatever.)
Last year, I kept telling my sister-in-law that it was bitterly cold here - it was only 70. Considering it was 10 degrees up there, she told me to shove off!
So do consider that. When you see the forecast for 70 or 65, that can be chilly to us. Or nice and warm for you! It all depends on where you are from. But I pretty much left all my cudle-duds underwear up north. If you do consider underwear, they are the way to go! They saved me in Chicago, especially during days when I had to wait for the EL in the dead of winter.
Two shoe stories for ya:
I traveled to Chicago, and since I really don't wear closed toed shoes or own many socks anymore, I brought sandals and a pair of open toed shoes because mom told me it was around 70/80. HAHA!!!!

My feet were SO COLD (got up to 80, mind you), that I HAD to buy new shoes!
And Uggs are really nice. They can be spency, but I love mine. They go great with leggings and a thin pair of ankle socks. SO toasty.