A couple of things here.
Wind chill. I always get a kick out of this. I swear its just something the weather people came up with to make those who dont live outside to feel colder and to tighten their grip on the masses stuck inside glued to the tube. OH MY TODD! Its only 28 outside but it feels like 100 below! Cut me a break! They had to come up with the heat index for the summer time so you'd feel hotter. This stuff is all for the consumption of those who live inside all the time.
Winter clothing. Anyone who works or lives outdoors knows that dressing properly is the key and what your level of activity is, dictates how you dress. Layers are everything, no matter what your level and you adjust that as your temps demand. I'm active most of the time, so I dont wear as much as my partner who stands still most of the time. Where your gun(s) fits in all this depends on your normal mode of carry and how you practice with it. I always have one where it always is, everyday of the year. It tends to keep things a lot more simple and another layer of or two of light clothes over it doesnt change the draw much if at all. A big, heavy parka on the other hand will. It will also be impossible to ever be comfortable with it on.
Gloves vs. Mittens. I have to work in cold weather every day and I need the dexterity of my bare hands for a good bit of what I do. Gloves dont make it, they are to bulky, even the lightest ones offer you poor dexterity, and they really dont keep you hands warm. They separate your fingers from the rest of your hand so you CANT keep them warm. Mittens on the other hand (so to speak
) allow you to keep "meat on meat" and keep your hands warm. Just having a front "pass through" pocket, like on most anoraks will also allow you to keep your hands pretty warm just by popping them in and holding on to each other. Mittens of the right size and type come right off like a hockey players gloves in a fight. You dont really have to pull on them, just drop your hands quickly. For me this works, because I clear my sweatshirt/fleece/anorak by sliding my palm up my pant leg, thumb up, under the edge of them as I lift up. I can clear whatever I'm wearing, even multiple layers, very easy this way and all with one hand. I can also do it pretty damn quick and all in one motion from mitten off to gun out. You wont do that with a pair of winter gloves.
cold metal and sticking flesh. My hands are often wet from sweating in the mittens(they can be that warm) when I throw them off. We use a large steel stake to drive holes in the ground so we can put stakes in. Its outside with everything else and I've yet to have it stick to my bare hands when I grab it. I seriously doubt your hand will stick to a pistol left in an outer pocket. Its not going to be anywhere near cold enough, especially with your body heat under it to stick to your hand. Now if you put your tongue or wet hand on a flagpole or handrail, thats on you, but unless its been sitting out by itself hours on end in sub zero weather, its not going to be much, if any of a problem.
If you use some common sense and actually practice with what you choose to do, I doubt you'll have any troubles. Then again, if your exposure to the weather is what you encounter from the house to the car and then from the car to the office, regardless the time of year. Your probably not going to be dressed right and your most certainly not going to be happy if the car breaks down somewhere in between, especially if its rural like around here.