What shoes do you have? I wear the Sidi Winter Boots.
How cold is it where you ride? Winter temps are 30s and 40s, pretty much always wet wet wet.
How much more time can you spend riding in that temp. because of your shoes? Lots. I couldn't ride in the winter if I didn't have waterproof shoes. I have Raynaud's Syndrome very badly, and it's imperative that I keep my feet dry.
How do they fit (relative to anything, like Sidis, like Birkenstocks, like other cycle shoes, or other street shoes)? The Winter boots are men's only. SO, while you still buy the same size for length, the VOLUME is greater. This actually turned out to be a really good thing. Although they feel really big if you try them on with regular socks, in practive I never wear them with regular socks. (see next question)
Do you also have extra insoles or booties or other tricks up your sleeve (or your sock)? I swapped out the thin liners for a pair of Australian Shearling insoles (sooooooo warm), and I wear wool socks with chemical toe warmers on TOP of my feet. With all that in there, the volume is totally filled up (even a tad snug), but my feet stay much warmer.
Anything else? The boots are fully waterproof. BUT your feet will only stay dry if you prevent the water from getting in the top, by wicking down your tights to your socks. In real rain, I wear fully waterproof Goretex rain pants, with the tops of the pants firmly secured OVER the top of the shoes to keep the rain out. In light mist, or wet road conditions, I wear backpacking gaiters. This protects my calves and prevents the road spray from getting my tights and socks wet.
If you DO get caught out in a big rainstorm without pants or gaiters, the water will wick down your tights straight into the boots. Then the boots act like buckets, and will keep the water inside fully. You'll be able to dump them out when you are done. Remember, Goretex is not directional. If you fill up the shoe with water, it won't "leak" out! :-)
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