I'm in the same area you are, and a bit of a winter wimp, at least in comparison to all these guys from up north. They'll be wearing shorts in weather that gets me bundled up. I was out for a group ride last night when it was in the low 50s to high 40s. Here's what I had on:

Fleece lined tights
medium wool socks
long sleeve fleece lined jersey
windbreaker
Long fingered gloves with a pull out "lobster cover"

I was slightly chilly for the first 3 or 4 miles, but after a couple of modest hills I was quite toasty. About 9:30 I pulled out the covers on my gloves and that got my fingers perfect. Toes were a bit cold and I thought I should have brought the toe covers, but it wasn't anything really unpleasant.

Coldest I have been out riding was about 42° last winter. The fingers and toes were the only things that I had a problem with after a few miles. I need to improve my gloves and fgootwear.

The folks from up north will find that extreme overkill, but it reverses in the summer when we are riding in 110° weather and we don't think anything of it. Heck, 95 was like a cold snap just a few weeks ago.