I wish I could remember what temperature it was last winter in San Diego when I pulled out my wool pea coat, scarf, and mittens. I suspect it was in the 40s or 50s, I know it was January because I was still working at my old university job. Our receptionist always laughed when I arrived in the morning because she had just returned from a winter trip to Germany.
I figured it would take me a full year to adjust to Milwaukee winters, but it ends up that I just needed a couple of arctic blasts. We had a major thaw this week with the warmest day getting up to 59 degrees. In San Diego I would have been pretty bundled up at that temperature -- at least a sweatshirt, probably a scarf and, in the evenings, maybe even fleece-lined jeans. Definitely socks.
What did I wear here? A t-shirt, thin cotton capris, and sandals. And it still seemed too hot!