The worst for me isn't all that bad. It was just a water situation for me. It was about 96F or abouts. I carried two 24 oz bottles, a 32 oz bottle, two 20 oz Gatorade, and at the only store we came across I bought 2 more bottles of water and a Gatorade. 10 miles to go and I ran out of liquids. I sweat, a LOT. When I got back to the car, I was bone dry, chilled, and shivering in 96° and 99% humidity.
Coldest I've ridden so far was a few weeks ago at 22F. I was toasty warm except for my toes and fingertips. I had ski gloves on and my shoes are ventilated and had regular cotton athletic socks on. I've since received wool socks for Christmas, but haven't had a chance to really test them. At 28° I was fine with my shoes being ventilated and regular socks on.