For over 20 years I rode with a Widder vest and Widder gloves in cooler weather. My worst trip was on the Blackbird, coming back from having some aux lights prototyped at The Electrical Connection in Knoxville TN. Took most of the day to fabricate the metal bracket, the harness, and install it, as Lewis was looking for a Blackbird to make a pattern for it. It was February, and thus getting dark once it was all done. No hand protection on the 1100XX, no heated grips, but I had my Widder gear... no problem, right?
Well, it really WAS a problem, because the temps were headed to the low 20s, and I swear I must have stopped at every flipping interstate Waffle House between Knoxville and Birmingham, to get out of the wind and drink some hot coffee. It was a LOOOON-NNNNG cold ride. As mentioned, it was sometimes difficult to undo the D-rings on the helmet when I got off the bike. My hands were taking a beating.
After a couple of decades the wiring began to fray, so I repaired the connections a few times, and finally upgraded (Pat Widder had retired by that time) to Warm and Safe, a jacket liner and gloves. This jacket actually has long sleeves, and the gloves are much less cumbersome and more flexible, and altogether more modern and updated. I have the wiring on the ST1300 as well as the GSA, which has surprisingly good wind protection. AND handguards, so much easier to add the new style Hippo Hands -- which are amazingly effective in their own right. They just don't work as well on the ST, as there are no handguards to keep them off the levers.
Even with heated grips (and seat), my hands will get cold in the 30s, so the WnS gloves are most welcome.
Also as mentioned, the jacket liner is best worn over a thin layer to be close to the skin. That's a little annoying, because putting on a long-sleeved shirt over the jacket liner means I may have to remove my shirt, then the liner, when I get to where I'm going. But for riding, it's a great setup. I add whatever insulating layers I wish over the jacket liner, depending on how cold it is. I have several riding jackets which are adequate alone over the jacket liner which is over a long-sleeved t-shirt or a winter base layer.
Fleece neck gaiter, or full balaclava, depending on need.
The tops of my thighs are what gets cold first in the worst of the cold here, so cold weather base layer under street pants, with riding pants over all that, prevents that. I don't think I want to mess with heated chaps or pants liners or even socks. My feet rarely get cold while riding.
At my age I don't feel the need to prove anything to anyone anymore, so I have no qualms on repeating myself... don't stop me, even if you've heard this before: "I HATE being cold!" And with a reasonable budget, appropriate priorities (motorcycle!), we have the technology available such that there's no reason to suffer due to freezing temperatures.
In the end, if I'm traveling this time of year, I'm wearing electrics, and I'm packing adequate layers in case the power dies. It's 12v, so if it really does die, I'll likely have additional issues to deal with. (Why won't this bike start...?)
I'm not a competitor in the Paul CB Memorial Ride. I've only ridden at 29 degrees thus far. It won't get below zero F. here in most years.