This was me last night. First night time ride of new season. Low of 57 degrees out at 8:30pm. I'll have to get used to the routine again and experiment to find what works best at what temps. I'm 5' 7" 137lbs and get cold toes pretty easily on night rides once I get into the mountains.

Last night the outfit was:
Sugoi RS Bib knickers
Defeet Wool socks, medium thickness (not the wooly booley)
Northwave shoes with ghetto duck tape on the toes
Craft zero t-shirt base layer
Short sleeve jersey
Neon Yellow PI vest
Descente Arm Warmers
Assos early Winter gloves
Craft windstop beanie

I wish I could get away with just wool socks for the temps in the Bay Area but it usually ends up being a combo of that plus the toe warmers and some sort of shoe cover. My core was plenty warm last night but the toes started to get cold once I got higher up on my regular climbs.