Hi Look,

Congrats on getting back to riding! Like you, I'm in the upper midwest, and dang, it gets COLD here.

I can ride down into the 50s with just basic biking tights, a shirt/jersey, and a windbreaker. I carry long and short fingered gloves, and change as needed.

I can ride comfortably in the mid 30s with long fingered gloves, a skull cap thingy under my helmet (for my head and ears; I found one in the runners section of a local sports type store), long johns under my tights and jersey (I'm a beginner and don't have arm warmers), and the same windbreaker. The skull cap thing makes a HUGE difference to me. I also change to heavier and longer wool socks. I keep warm as long as I keep moving.

Below the mid-30s, I'm a whuss. I would probably need something for my face and shoe covers, and glove liners. But I'm unwilling to be that cold, so I put my bike on a trainer.

So, I'd prioritize: long fingered gloves, skull cap, as the first things. Long johns/base layer, well, if you're in Wisconsin, you probably have those already. I find the "tech" type better for riding than the comfy silk type.

Good luck, I hope you have lots of fun riding.