Dont deviate from your vans? That wont work very well once the wet and snow comes, your shoes will get wet, freeze, make your feet cold as hell and your toes are gunna get frostbiten and fall off! You really shouldnt wear two pairs of socks, I hear it reduces and restricts blood flow, not to mention your feet going numb sometimes isnt good either. One pair of wool socks are fine, if not, a very thin pair of socks(like a base layer)should go under them to keep your feet warmer and wick away the moisture that makes your feet cold.
Idk about boots and toe clip riding, I usually take mine off during winter months as I dont want to get trapped in them if I fall or have to jump off the bike for any reason. Plus they dont work very well with boots. I have enormously big feet as it is with shoes, once I add boots to the mix, game off, toe clips wont even fit me. I would just say find a pair that will keep your feet dry and warm, wont reduce your pedal stroke by much and that fit your clips, or a new pair of XL clips for the season.
hey Jen P., are you from the south side? I think they are the only people who call Jewel Jewels..
I like Jule's idea about the waterproof hiking or running shoes
I use the Lake cycling boots with wool socks. As long as I keep the leather treated I can ride around in the snow and rain all day and my feet stay dry and warm. I need to ride all winter/all day, so this works well for me. I ride clipless but these would work with clips as well.
I highly recommend the 95% wool/angora socks that Rivendell sells!