Do you hate winter?
Are you always cold?
Do your fingers turn funny colors in the cold?
Have you been rescued mid-ride because you lost the ability to brake or steer or do other key things due to numbness and/or shaking?
This is me, unfortunately. I used to just hate the cold. Especially after I moved away from Vermont, where the prettiness outweighed the fact that it was -20. In Pittsburgh I got away with not riding outside in the cold, because there was slush or ice all the time, it was dangerous at baseline to ride in that city, and I only had a road bike. Flash forward and with gravel and much less precipitation in the mid-south, I found myself with no excuse. And subsequently entered mild hypothermia territory a few too many times.
Through trial & hypothermia, I finally feel good about my ability to not die whilst riding a bike when the temp dips below forty. And while I still wouldn't say I love winter riding, it has more to do with the fact that it takes so long to put on all this darn stuff than the actual temperature.
1. Bar Mitts
These giant, dorky, neoprene things are my best friends. They create tiny warm houses for your hands. No matter what gloves, mittens, or glittens I tried, nothing has ever kept my hands warm below forty while biking or running. I put these on my bike for the first time last winter and immediately did a 50 mile ride in the high 30s. I have used them down to 20s with a normal pair of gloves on. My hands may be Reynaud's-y to start, but once some heat accumulates (or with the addition of hand warmers at the start), they'll regain circulation and stay that way. The downside is obviously limited access to your bars. I can comfortably hold my hoods and brake, but can't really grab the drops, even over the bar mitts due to the shape of the neoprene (it doesn't exactly collapse under your hands). Additionally, if the temp warms up, it's not exactly easy to transport them home if you remove them. Way too big and bulky for jersey pockets or your average top tube/bar bag.
2. Pogie Lites
Enter Pogie Lites. The fine folks at Bike Iowa make them, so supporting Bike Iowa is the first plus. These solve the problem of access to all parts of your bars, and also being able to pull them off, roll them up, and stick them in your pocket.
They keep my hands much warmer than I expected. I used these at Spotted Horse, where it was 30s-40s and raining the whole day, with a pair of mechanic's gloves and surgical glove base layer under them. My hands got numb-ish a few times but remained functional and out of the painful-numb zone. For a cold-handed person, they thrive between 40 and 50 degrees, but are workable down to 30. I happened to only have these on a 22 degree icy ride in Stillwater in November, and they were insufficient. There was a bail-out followed by a painful rewarming. Overall I love them for the versatility and convenience as long as it's not ridiculously cold out.
3. Lake Cycling Boots