Get a knit beanie that you like. I have a Marmot with a fleece band stitched to the inside that is superb. I also have an FMF (powersports exhaust) logowear beanie that I must've picked up on some deep discount years ago. It has proven remarkably competent this winter, with impressive wicking capabilities. I watched the precipitation change from rain to snow on Christmas morning, and it did great all week. I have less hair than you, but in relevant conditions (still well above freezing), I'd rather have a t-shirt and a beanie than a jacket and nothing on my head.
I haven't seen it mentioned yet, but when I lived near mountains and spent extended time outdoors in snow, I really liked silk long johns as a base layer. Even better than wool. But I don't bother unless I plan to be outdoors (or possibly outdoors) in snow all day.
I'm good down to the mid 30s as long as I'm active and it's a relatively dry cold with just an insulated Dickies "Eisenhower" jacket. If I'm going to be less active or out for a longer period of time, I do more.
My basic building block is a "down sweater," basically a lightweight down jacket. Has a big, tall collar that does the job of a scarf really well. It weighs almost nothing and packs down to about the size of a softball if you need to do that. Amazingly warm. I picked it up on an end of season clearance for about $50 at the local REI nearly a decade ago. Over that, depending on conditions (rain, snow, wind, etc., I have an REI brand Gore-Tex shell that I bought in 1996 and has been almost everywhere with me. Still going strong, although if I used it more or harder, I probably would have killed it and replaced it with something tougher. If needed, I'll add a first underlayer, something like a thin fleece. With that, I can be outside and not super active for a couple hours down to about 20. If I'm active, I might sweat even at that temp.
I haven't had any reason to be out much colder than that in recent years, as the (work) equipment I use starts having issues. Replacing the Gore-Tex shell with a decent quality winter parka gets me down to zero or so. At that point, you need to pay attention to exposed skin. I took my usual 40-minute walk last February when it was about 6 here for a couple days, and I think I damaged the skin on my lip a little bit. Some kind of wind protection would have been good. That's when I revived
this thread. I still "need" to do something there, although I haven't actually "needed" to yet.
Since you're a Milwaukee guy, you might at least check out their line of M12 heated gear.