For me, footwear is very simple: 1. Waterproof, 2. Layers. If you ride clipless, there are more winter shoes coming out from companies like Shimano, 45Nrth, and Lake. In the past, they never held up through my winter thrashing but the new models look like they are constructed better. If you can swallow the hefty price tag (45Nrth Wovhammers run $325) and want to have a very specific shoe (I would not want to shovel the snow with a cleat at the bottom of my foot), then these shoes would be good for you.
I personally prefer having a nice leather hiking boot big enough for adding layers. Hiking boots are made to flex while add support as you hike around in different terrain, which helps as you pedal along. Other taller boots can be a bit heavy and hinder flexibility. I’ve been using a pair of Merrel Original Wilderness boots and Jeff just got himself set of Hanwags. These are both pricey shoes, but I use my boot in the summer for hiking so I get my penny’s worth out of them. What’s also so great about them is the unbelievable amount of traction they have. So not only are they comfortable in the winter, they are perfect for doing everything else you do in your life. Plus, I really like how these boots look.
The natural waterproof characteristic of leather really helps keep your feet warm and dry. Just make sure if you are purchasing a new boot that there are few seams by the toes. You’ll be surprised how much cool air can drift in between the threads. Also, just like your bike, take care of your boots. My Dad taught me to polish and care to my leather shoes at a very young age, one important lesson to keep if you want your nice stuff to last.
As for insulation, I apply the same rule as I do with my pants and tops: Wool Layers. Having a very simple boot allows me to add and subtract socks according to the temperature. Around 30 Deg I just wear a medium wool weight sock. Below 0 Deg, I throw on a medium sock over a lightweight one and I top it off with a windproof Goretex layer (pic above). According to “The Converse Guide fot the Outdorsman,” there’s something about layering thinner socks versus just wearing one big sock. Once I tried it, I never went back.
To add more insulation and waterproofness, try out gaters. They cover up the top of your shoe so that if you were to step into a heap of snow, your socks will be free of water. I also carry an extra set of socks with me on longer rides. Having so many layers can build up some sweat which can turn cold if you are out for a long period of time.
I’m all about purchasing things that have more than one use and that are made to last. I use all of these pieces throughout the year in different conditions. Remember, quality can be the difference between a horrible ride and a really nice one as well as having something for a lifetime or for a season.