When I'm out hiking with my backpack and boots, I always wear my Zip-Neck 240 during the cold months. It's great as a transition and with a T-OSS 135 underneath, I can easily regulate the temperature, which can vary whether it's uphill or downhill. Even though I get warm and damp, I don't feel cold and the clothes dry quickly without becoming stiff or uncomfortable.
On both long and short runs, I always wear my long-sleeved T-OLS 220 throughout the winter. It provides super comfortable clothing that doesn't get sticky or clammy. But most importantly, I don't get chilled by the wind and weather, even though you can be wet with sweat.