If the roads are reasonably dry, I tend to push the edges of the seasons and get out there when it's pretty cold. So far this has been a pretty dry winter and I'm still getting out on rides into December despite the new zwift setup.
The thing is it's hard to be comfortable when it's in the 30s and that kind of means a lot of specialized winter bike clothing. What I find most important is keeping my hands and feet warm. Then wear a warm enough jacket and you'll probably be ok for a little while at least. A buff/neck warmer is also a big must have. From there it all kind of gets optional.
Until this year my go to setup was a pair of hand me down 45nrth fasterkatts a size too big, running tights over regular bib shorts, and a softshell jacket that seems to be meant for running and xc skiing. it's fairly slim fitting, or was when I got it, but now it's a bit flappy. My gloves were pearl izumi softshells that are pretty warm, but have some holes in them now and the padding in the palms is annoying and adds unnecessary bulk. So it was all kind of patched together, but worked well enough.
Thanks to working at MBW this year I had a little extra cash plus some pretty good discounts and decided I needed to get some better stuff for winter.
Firstly, bib tights. I've wanted some of these for awhile and now that I have some I'm wondering what I was thinking just doing tights over bibs or leg warmers for all these years. They're super warm and cozy and so much better. The ones I have are pearl izumi amfibs, but there are plenty of similar ones out there. I want another pair so I can ride more between loads of laundry.
Probably more important are the shoes. I went with shimano's MW7 goretex shoe and they are really warm. I've seen sub 20f, and been out for 4 hours in below freezing weather and my toes were happy the whole time. I'm surprised at how much warmer these are than the fasterkatts, and they have a nice flap over the top to keep water and grime out of the tongue and boa laces. My only problem right now is there's a small gap between the bottom of the tight and the top of the shoe, so your sock gets wet and then eventually there's water in the waterproof shoe. I'm thinking I need some little flaps or sleeves or something that I can have under the tight and over the top of the shoe.