Baby wearing in winter
Oh it's easy to wear baby in winter! If you have a jacket a wee big, you can just zip in around baby too, just not all the way over the head. Put a warm Cheap Snapbacks hat on baby and may a scarf if needed. I always took cues from babies feet/ankles, if that was cool I would tuck a blanket around baby as well. There were times when it was nice when we went in a store then on the way back it cooled off and I wrapped baby with a blanket tucked into the straps and me with no jacket, but a warm babe on my tummy I could easily make it to the car. I even found a tutorial for making a a pocket in the back of a jacket/coat for a back carry. Very clever. You can find it on pinterest or the baby wearer forums.
I have one born Jan and one in Oct and I live in New England. I would just button my coat around them, it kept the nice and toasty. I was more concerned with overheating. Between the down coat and all the body heat, it got pretty toasty. YDS would wear just fleece footy pj's. On his little head we would either do an infant balaclava or a good hat. Or both. Our chi hair straighteners coldest walk was 7F and we were out for a while. Maybe an hour. He was still toasty with just what I said above, plus a onsie and baby legs on under the footies.
Just wear LO in a popable carry. Stretchies are great for this and tend to be very warm as well. Pre tie before leaving the house and just put your coat on over top. You don't actually have to untie it after you take LO out. I would just drive around with my wrap on. Nobody wants to take time to wrap without a coat in the cold. There are popable carries in wovens as well, and some nice warm blends. You can find nice thick wool wraps. RS's are nice too, but less warm. I do like them for nursing while wearing.
Oh, Wholesale Snapbacks Hats and I had no issues with wearing and I don't use an infant seat. We put YDS chi hair straightener straight into a convertible. The 5 seconds between wrap and car seat didn't bother him. We would keep a nice blanket in the car and toss it on him after he was in. If he woke up when we took him out, wearing him plus some BFing would knock him right back out again.