Originally Posted by tjspiel

For cold you want the outer layer to be something that's going to stop the wind, so I'd definitely choose the wind breaker over the jersey unless the jersey is wind proof. Jersey might be OK as a middle layer. Not sure what order you're using for the lower body layers but it sounds like you have plenty of them. The rule is pretty straight forward. The "base" layer is thin and snug fitting. It's meant to wick away moisture. The middle layer is thicker (though not bulky) and should be insulating. Fleece is great for this. Again, the outer layer's role is to stop the wind.

If anything you'll probably discover than for those temps you don't need to worry too much.