Boot suggestion for a NE Winter?

native, approaching my first winter in Boston. Use case: commuting (~10 minute bike, or ~10 minute walk to subway/bus) & walking around urban center. I currently have sneakers/running shoes, derbies, work boots, and (cowboy) boots , remember?). (none lined) Do I need to get a pair of lined boots AND a waterproof pair? Should I look for a waterproof pair w/lining (i.e. just get bean boots)? Will I be ok with just wool socks & work boots, or will it get cold enough that I’ll definitely need a lined pair? Do y’all have a dedicated pair of rain boots + your winter boots? Looking for recommendations for waterproof &/or lined boots, the one’s I’ve googled for so far have been pretty super ugly (in my completely super subjective opinion; I mainly dislike how distinctly separate the sole and upper of duck boots and other boots marketed for their “waterproofness” are. Is this an unavoidable side effect of the construction?) I’ve heard Sorel is good, any other brand recs? Open to a work boot/Chelsea, but also a chunkier more traditional winter/hiking boot as well .