Thermal Hand Socks (cool-weather gardener gloves from Lee Valley part #AH139 - no longer available) oversized so they are easier to put on and not tight
The NEOS overshoes were not warm enough at -5C or 23F until I used an antiperspirant. My feet are now warm at -30C or -22F (including windchill). In winter 2014/15 I stopped using antiperspirant on my feet. Because I added a wind shield to my handlebars, I didn't need to use antiperspirant on my hands.
I wear size 47 in winter and size 43 cycling shoes in summer.
On warmer winter days (-5C and above) when my NEOS overshoes are overkill I wear XXL DryGuy overshoes over my size 47 winter cycling shoes. DryGuy are lighter and waterproof but are no longer made.
On warmer winter days (-5C and above) when my NEOS overshoes are overkill, the roads are dry and I want to go clipless, I put on custom felt toe and heel covers velcroed in place and covered with XXL MEC cycling shoe covers (no longer available).
In the warmer winter weather and my face is exposed, I wear All-Sport Non-Freeze Face Protector SPF 30 by Kiehl's or Banana Boat Sport Performance Sunscreen Stick SPF 50.
If your balaclava or face protection does not stay in place, try "It Stays" Body Adhesive. You can get it at well.ca in Guelph, Ontario. Another product to try is Flash Tape body clothing tape by Brazabra. You can buy it at Shoppers Drug Mart.
White petroleum jelly can be used to protect your face from the cold (but not when it is really cold).
I wear two insoles sewn together:
The Insolator insole 3/8" thick/one size fits all/made with Cambrelle+Themolite+Neoprene/Men's 12-13 $8.50 (aluminum side down)
My winter cycling shoes are Shimano SH-M033 Gray SPD EU 47, US 12.5, CM 29.8. They are summer weight shoes and at least five years old.
When I wore winter boots by Kamik, I experienced discomfort in the soles of my feet after one hour. I need the stiffness of cycling shoes. As a result, I now wear cycling shoes inside overshoes.
What I take on long winter rides:
Extra mitts with caps and thermal hand socks
Face mask
Two polar fleece pieces to cover forehead, nose and cheeks
Two Heat factory disposal warm packs
Water in a thermos
Lightweight collapsible knapsack
Bicycle lock
Two bicycle tubes
Bicycle repair tools
RainShield O2 Cycling Series jacket if the weather could get significantly cooler (sometimes)
Homemade wrist mirror to ensure my inner balaclava is placed properly on my face and
to allow me to see traffic behind me
What I no longer use for long winter rides:
Hotronic foot warmers
Cycling jacket with sleeves (okay for short rides)
Cycling helmet cover
Cycling tights
Polar fleece ear covers that attach to the helmet straps
GORE-TEX products
Long-sleeved cycling jackets for longer than 1/2 hour (in cool or cold weather). I want as much perspiration as possible to escape through the arm openings.