I have struggled with that since I moved to NC in 1998! I grew up in New England where October means putting on flannel, bright leaves changing, and cool temps (and occasional ice storms ) In NC, fall clothing is something else entirely. I can survive most of the winter here without a coat if I want (I commute by car and park across the street so at most I'd have 10 minutes outdoors - a sweater is almost always plenty)

At the same time, I'm pre-conditioned to put away linen and certain colors in September. So I usually spend the next two months wearing sleeveless black cotton dresses