DVCFan hit the nail on the head: I actually prefer running in temps in the 30s & 40s, which is why I choose to run this race every year, so that I can train in the cooler temps. Notice, I've only run the W&D HM once, because it required me to start training in mid-August, which is sweltering hot here in VA. Not ideal, to say the least.
Thankfully, I packed many different layers for the PHMW races this year, but they still didn't help much, especially the morning of the 5K. I was dressed in a sports bra, running tank, long sleeved shirt, zip-up, cotton t-shirt, leggings, running shorts, and a windbreaker with a scarf & gloves. I looked like the kid from A Christmas Story. We were on the bus by 4:15am, and waited around shivering for over two hours since we were in Corral C. We tried everything to stay warm, from pacing around the parking lot, jogging in place, dancing along with the DJ, to drinking hot cocoa. Nothing really helped, and it still felt like my feet were going to snap off once we crossed the start line. We finally warmed up a bit just as we crossed the finish line, but we still grabbed the mylar blankets, because we knew that our sweat was going to get chilly quickly as we headed back to the bus to our resort.
Two days later at the Half on the other hand, I wore a sports bra, running tank, zip-up, and a running skirt with my tutu over it, and it was perfect.