Lisa -- if you can handle riding any distance at all in 23 degrees F, you are a winter rider! Below 32 is tough, that's where bad things can start happening, like body parts falling off. Down to freezing is merely a matter of suffering, that's the worst that can happen to you if you don't dress right & actual temps are still above the freezing mark. But below freezing, all bets are off.

About your fingers and toes, I will throw in my 2 cents worth. They work directly opposite. Gloves should fit snug, and shoes or boots should fit loose. Make sure after your sock layers that you can still wiggle your toes so you can do that while you're riding to check on circulation, and you still have room for a small cushion of air. Glove layers need to be close, so if you're wearing men's or unisex, make sure they're not too big on you, or too stiff that you can't make a fist easily, which you can do while riding to check on circulation there. Keep checking at least every 10 minutes, and if your face is exposed to wind, make sure you can still move your facial muscles.

My toe problem I've fixed now -- I ride with heavy-duty Lake winter boots and a heavy merino wool sock, a light-weight sock as a liner if it's below 20. My hubby got me a 3-layer glove system with wind-stopper on 2 layers that I've taken down to 21. I also use a thick ski glove with liners, but I don't like that as much because my hands get clammy & sweaty, then I get cold.

One other thought for you -- maybe your core isn't as warm as you think. I don't know how you are layering, but the body goes into defensive mode in extreme temps. It will send out signals to protect the head & the core above everything else. So if you are sweating & getting a chill on your core, the body might be sending out signals to cut off blood flow to your hands & feet because it sees the extremities as unimportant to its survival. Sounds like you've got lots of protection for your head. But how about your jacket? Do you have windstopper on your outer layer? I find that makes a huge difference.

Anyway, glad to see winter cold isn't stopping you from riding! You're a tough rider!