Do these keep your feet warm in the winter?

I don’t know what’s different about these but they are the only pair of boots that kept my feet warm. I jumped from wearing red wings for 15 years to carhart.

Does the boot go above the ankle? Are they warm in 20 degree weather?

This boot will be above the ankle for most wearers. It is not insulated, only waterproof. We do have insulated styles for more extreme cold conditions: CME8347, CMR8959, and CMC1259. Thank you

I'm a professional detailer and chemicals ruin all my other work boots. Does anyone know if the whole shoe is chemical resistant?

Yes they will hold up! Especially the soles. Ours have lasted almost 2 years so far & though they are finally looking warn out they are still comfortable. I getting new ones anyway in black this time because hard work deserves a new pair of shoes at least every 2 years! I want some that look good on the outside still. Didn't need insoles with these either! Great boots