One of my major limits for cold weather riding is cold toes. At this point I have 2 different hacks going. Above are the Lake MXZ302-X boots which I bought only after they came out in a wide size in 2008. (Even these are narrower than my feet, so I bought a size or 2 larger than would be ideal.) I use these on SlushBike and the MTB, and they're pretty good. But after the first season some heel stitching fell off, which I attribute to a design defect, so even after Lake re-stitched them for me, I added tougher stitching which you can see in the shape of an "M" above. The insoles are made of bubblewrap, too, which might be warm but which pops and falls apart. These are surprising problems coming from what looks like a mature shoe company.
Below are Keen boots I modified before I heard the Lakes were going to be available in a wide model. Here I made plates of 1/4" aluminum, cut away the soles under the plates so they'd be close to flush, and assembled it. The plates are for mounting the pedal cleat, as well as stiffening the boot for pedalling efficiency. I use this on my 'summer' bike, which uses Bebop pedals, allowing me to ride it down to around freezing. (This bike cannot use studded tires, so I wouldn't want to ride it much below freezing anyway.) I sewed the gaiters for wind protection and visibility. (I took pictures of this project, but can't find them now.)