Clipless shoes and winter tend to be a recipe for cold feet, especially when winter is spelled with a capital W.

Insulated hiking boots, shoes, or winter boots on flat pedals is really effective at 17... my insulated Merrell shoes handle this well and then it's boot time.

A good rule of thumb is that, if your clothing is too warm for walking about it is going to be much too warm for cycling... a wicking base layer, adequate insulation, and a wind stopping layer go a long ways toward being comfortable.