I live in the Canadian Prairies (Saskatchewan) and it gets COLD here. My go-tos:
- Wool trail socks (I get mine at Costco but they do wear out every year). These go up over top of my base layer pants
- Insulated Bog boots (good to -20) or Kamik winter boots for colder days
- Paradox base layers for really cold days (top and bottoms again from Costco)
- Fleece lined riding tights (I have Kerrits)
- Carhartt fleece lined work pants
- ski pants for REALLY cold days
- Tank top/undershirt
- Paradox base layer or other long sleeve wool shirt
- vest (I have a packable down for warmer days and a Canada goose down for cold days). I also have a heated vest for days when I will be outside for hours on end.
- Marmot brand down filled coat that goes past my bum for cold days OR packable down coat for warmer days
- Fleece lined gloves (SSG brand) or fleece lined mitts (the Bay olympic collection) for warmer days OR I have a pair of heavy duty mitts that have individual fingers inside but are a mitten on the outside for really cold days. I also have a pair of heated glove liners for really cold days when I’ll be outside for a long time.
- Watuko winter extreme gater (like this: https://www.watukoheadgear.com/product-page/winter-extreme-gator-171) with another scarf on top if really cold
- fleece headband (can go under helmet)
- fleece lined toque
Typing that all out… it’s all about the layers. I also keep spare gloves, scarfs, and hats along with a blanket in my vehicle just in case and my locker at the barn has spares of the above plus socks, leggings, tank top, and mid-weight coat to change into if I get wet to the bone.