I do love Carhartt. One of the first workwear pieces of clothing I bought was a Carhartt chore coat and I’ve worn it almost every day since! Size them to fit over your flannels and sweatshirts, find them here and pair them with a good set of leather gloves. Something to cut the wind that you can actually use too.
And Columbiaknit. I could have easily just said “Carhartt beanie” and moved on but CK stocking caps need to hit the scene. Made in America and they’re really high quality. These are my favorite.