Originally Posted by
WhyFi
I don't think that you're going to get any meaningful insight from others - tolerance to cold, 'specially when it comes to extremities, varies quite a bit from person to person; some people "need" gloves at 60°F while others will go bare-handed at freezing or slightly below. This is one of those things that you'll just have to try, though I agree with the basic premise that winter shoes/boots are more convenient than booties (though I still haven't found a good winter shoe/boot for myself, unfortunately).
Agreed. I'm one of those whose toes and fingers have very low tolerance to the cold. Just like other parts of your body, layering is key. Summer riding I'll ride with summer shoes without insoles. Come September I'll put on thicker socks. October--back to thin socks with neoprene booties. Late October--thicker socks with booties. November--Defroster boots with regular socks. December--Defroster with thicker socks. January and February--when it's -10*C or colder, chemical warming pack with thick socks, Defroster boots, and neoprene booties. This is okay for a couple of hours, but the chemical heat pack stops working after a short while due to the lack of oxygen inside the shoes.
You have to experiment on your own to see what you can tolerate at different temps.