The wind-proof stuff goes on the outside, just like everywhere else.

You wouldn't wear a windproof undershirt, then your insulating layers on the outside, right? The wind would blow the heat all away. No, you wear a wicking undershirt, insulating layers, then the windproof jacket on the outside. Same for your feet. Wind/waterproof layer on the outside, insulating layers inside.

I'm with Leebo. You're expecting too much from shoes that are specifically designed to keep your feet cool. It's working, right?

Further, three-seasons shoes are designed to be worn tight. In winter, this squeezes out the blood flow that brings the heat to your feet. Compounding this, stuffing an insulating later in there further reduces circulation. And insulating layers are supposed to stay fluffy, not get all the air squoze out of them. They don't work when compressed.

It's probably too late in the season to re-do your footwear. For next year, think about a winter cycling shoe/boot. You don't have to go whole hog with the Lake MXZ303. I love my older 302s. Seven winters of toasty feet, even this year. I don't even bother with two pairs of socks until it's below zero.

There are others that are considerably less expensive, and probably make more sense for Memphis.

Winter cycling shoes are designed to keep your feet warm and dry. The cleat backing plate doesn't come all the way through the sole like on three-seasons shoes. Then with the insulated mid-sole and insole, you don't have the heat-sink effect of the cleat sucking warmth from your foot. Personally, I love clipless, and wouldn't ride any otehr way. This goes double-plus good in winter when slippery pedals make pedaling both a chore, and a pain when my feet slide off.

Whatever you buy, make sure it's a couple of (metric) sizes larger than you wear in the three-seasons. This keeps the loft in your insulated socks and such, which keeps that working, and it keeps the blood flowing to your feet.