Genetically we all handle cold differently, temperatures one person can barely handle, another flourishes in. Me personally, I can’t stand 80 degrees, even 75 can be too warm for me at times. While -20 is much more comfortable for me it’s even more bearable with the right gear on. By no means do I believe I have the ultimate winter setup, I’m still changing it up, but last year I made some major changes and dropped well over 20lbs of clothing in the process. From top to bottom: a beanie or baseball cap depending on temp(I have to remove it while mobile to prevent sweating) thin neck/sun gator with a fleece gator in a pocket in case the wind starts to bite, IDO Hoodie (warmest I’ve ever worn) wool sweater underneath if colder than -20 otherwise a reg hoodie underneath unless above 20 degrees, and under armor 4.0 as the only base. Legs get UA 4.0 and usually fleece sweatpants or jeans under the Ice Force Bibs. Boots are Cabelas Predator Extreme pac boots and while they are bulky (but not heavy), they keep my feet incredibly warm and dry without sweating. I wear one pair of poly/wool socks. I picked up some Frabil FXE gloves that keep the digits warm and in between use I bury them between the base layer tops and inner hoody to keep them warm and dry. The rest comes down to acclimation to the elements. The more time you spend being cold, the less you become effected by it. There are other things one could add to the list like hand warmers, drinking “hot-wets” (cocoa, tea, coffee, or just hot water) a quick warmer upper/circulation booster is a drop or two from a cayenne pepper tincture under the tongue. Most importantly, you don’t want anything to feel tight and avoid over-layering. Circulation inhibitors will keep you cold. My whole body, especially my back and hands, feel colder when my feet are cold. First thing I would do is play around with some warm-comfortable boots. Unless someone here has any other recommendations skip the trial and error and look specifically for Baffin Apex or Cabelas Predator, there are likely other comprable boots out there but these two are sure bets.