Temp.: 50 degrees (9C)
Wind: 15 mph and cold!
Terrain: Rolling hills
Distance: 4.5 miles
Did It Work: Yes. I was worried that I might have gone overboard with the under layer, but the strong, cold wind kept me perfectly balanced between cool and warm.
Note to self (and maybe you?): As long as key parts of me are warm enough, I am comfortable. Specifically, I hate having cold ears, hands and torso. When dressing for temps on the edge of cold, I always make sure I protect these parts first.