It's hard to measure the dryness of clothes in 55 degree, 70 percent humid weather -- unlike summer when it's easy because it's 100 degrees with no humidity and everything has no choice but to turn to a crisp after a few hours in the sun (including me). In hot weather, if your clothes are cool they are also inevitably damp. In cold weather, all the wash is cold, making it harder to tell if it's actually dry as well.
It's a strange dichotomy -- too humid outdoors, too dry indoors, but I'm sure anyone who lives in a coastal climate in winter can relate. Sometimes it can take awhile to fashion some new techniques to accommodate a new climate. In this case, we are entering our third year here, there are still some things I am figuring out.