I bought the 45North Fasterkatt boots a couple of winters ago. Expensive. Rated to about 20F which for Portland, OR riding, quite sufficient.

What a pleasure to wear and ride! Didn't know my feet could feel so nice on cold wet days. Rode 80 something miles the day of respite between winter storms. So, light rain at times, in the thirties and very wet roads. I had to ford several deep streams running across the road. Rode to and then about 5 miles on gravel logging roads to a falls, then back. The boots got a real test. Walking, wet, hard gravel riding (probably climbed a thousand feet) and 70 miles of road.

So my take is this - yes real winter boots are expensive and take years to pay off and justify. But they make riding in real winters fun! And they make dressing and undressing far easier that the home made systems.

I did make one improvement. Gaters. Special gators to keep water and cold out of the boots. I bought stretchy outdoor fabric and velco. They are about 7 inches high and fitted snugly to my ankle the top 3 inches and likewise to my boot the bottom 3 inches. Velco strips on each half. I wear them under my tights and over the boots. Cozy feet!

This after nearly 50 years of other "solutions". Why did I wait so long? (Well in part because 40 years ago, these options didn't exist n bike shops I went to, no internet, blah, blah blah ...)

Edit: The Fasterkatt is 45North's next to warmest boot. Warmest goes to 5F. Based on what I have seen, that is a real 5F.

Ben