My mesh upper cycling shoes with booties and wool socks are good for 40 minutes at about 10 below Fahrenheit. I think for colder temps or longer rides I'd start to have problems. I also replace the soles with insulated ones for winter and don't use the cleats (I take them off). If used clipless pedals in the winter, I imagine they'd not work as well since the metal cleat and screws are going to transfer more of the cold into the shoe. These are MTB shoes and they have a pretty substantial rubber sole which helps.

People are different though. What works OK for me may not for you.