I have no idea how you guys do it. I get it; I grew up in SoCal and spent only 4 years here in Tennessee, and I'm OK with the cold. But that GD windchill kills me. I absolutely CANNOT stay warm. At all. I can layer up till I can barely fit into my leather jacket: undershirt, long-sleeve cotton tee, sweatshirt, quilted hoodie, quilted leather jacket liner, leather jacket, headsock that covers the neck, Fieldsheer Aqua Sport gloves with silk glove liners... bottom half stays warm enough though. I guess it's mostly my hands. I'm thinking of getting the Gerbings Hybrid heated gloves. However, there HAS to be a cheaper solution than blowing $300 on gloves!
Anyhow, I digress... coldest was 30F, for half an hour. 40F = 40min of endurance. 50F = 50min. 55F and over--I'm good; can be out as long as my food holds out.