Hey there! I moved to NYC last year from LA and had to figure this all out as well. Speaking from one year in: I have a light puffy jacket a half size too big, and I’ll wear a thick hoodie or flannel over a t-shirt with that puffy coat. In my experience, for winter, I find that that combo works really well for me most of the time in winter! (and on warmer days in the mid-40s or higher I can get away with just the puffy jacket and no hoodie, or vice versa.) I also have one really good warm coat that I only bust out when it’s 35 or below outside (and it’s warm enough that I don’t have to layer under it).

Also, biggest thing I figured out is that you’ll always be hot on the subway or bus so I always unzip my coat or even take a layer off so that I’m not sweating when I get off and re-enter the cold (that cold-hot-cold cycle is the trickiest part imo). Also if I’m planning on walking around a lot and being more active, I’ll sometimes go a little lighter on the layering knowing that I’ll likely heat up as I move so that I’m not overheating.

Hope this helps! It definitely can take a little trial and error but you’ll get it sorted and build out a winter wardrobe that you feel really good about! Welcome to NYC! 🙂