Who cares what's on the outside--its the fleece under it all that counts
We've got a serious mis-match of things to keep us warm and (somewhat) dry. Our footwear sucks because we prefer to have traction on deck rather than dry feet--and we simply rely on high-tech sock liners and wool socks to make up for it, though. So you'll find both of us in soaking wet high-traction deck-shoes. Even so, from my (spring whitewater canoing, not sailing) experience, wet shoes with good high-tech sock liners and wool socks are warm enough unless the temperatures are under the low 40F range.
Best rain gear seems to be that marketed to the fishermen. Here's hubby in such gear. Sorry, don't recall the brand. Heavy stuff though. Note he's got on deck shoes.
Here I am in an old goretex winter parka with layers (yes, more than one layer) of Patagonia capilene expedition weight synthetic fleece under it. When it is really, really wet out, making sure that I'm covered in fleece under the outerwear is much more important than what's on top.