SoCal boy terrified of 34 degree morning ride

I'm one of those cyclist that has chronically frozen feet at pretty much any temperature below 64 degrees and sunny. So I'm basically [doomed]. Because I'm going to Solvang for a cold all day ride this weekend (why is it so cold up there?). Now, to be honest, it's just the low that's forecast at 34 but we are planning a very early start and the first 30 miles or so appear to be mostly downhill. So my idea is to dress warmly (good thinking!). And just suck up carrying the extra layers all day as it warms up to low sixties. Does humidity help or hurt me in a situation like this? It's going to be pretty wet/coastal and windy most of the day. So like I said… Here's my secret voodoo. Let me know if you approve. A liner sock with an inside out wool sock over it. Why inside out? Hmm, well, because I figure all those nice little nooks and crannies for air pockets will be better as insulation just off the skin. And I figure inside-out-ed-ness must attract some sympathy from the gods. My backup plan is a few shots of something warm in my jersey pocket…