1. The Woodlands Knit Caps
The Woodlands is located in Portland, and they have a great in-house line of stocking caps on offer. The three styles – the Chunky (three colors), the Cadet (three colors), and the Standard (four colors) – are all woven from 100% wool fibers. The Chunky and the Cadet come in contrasting fibers for a melange look; the Standard is all solids. The Chunky and the Cadet both have a heavy gauge knit, but the Cadet's longer length is designed to be worn rolled. The Standard is a medium gauge knit that will look great either rolled or flat.
2. Filson TIn Cloth Insulated Cap
Filson's tin cloth is a storied fabric known for being one of the very best options in rainy, cold weather. This cap has a tin cloth outer to keep your head dry in wet conditions and a hidden polyester lining that folds down to cover your ears when the temperatures drop.
3. Fairends Cadet Flannel Ball Cap
This Fairends cap may not have ear warmers, but it is made from a fuzzy wool flannel that is very winter appropriate. Fairends is based near Missoula, Montana, a great part of the world that certainly knows a thing or two about cold winters. This cap will be a good friend to many this winter.
4. Upstate Stock Fingerless Gloves
Hats not may be for everybody, but gloves are a must in winter. These fingerless ones from Upstate Stock are made in New York State from wool fibers. I see a lot of fingerless gloves, probably in part due to the rise of the touch screen phone. However, they're valuable even if you're not trying to make video calls outside, and allow some more fine motor control than bulkier gloves.
5. Geier Lined Deerskin Gloves
If anyone's looking to step up to a pair of heavy-duty gloves, look no further than these Geier lined deerskin ones. Deerskin gloves are soft to the touch and hard-wearing, and with an insulated pair you'll be daring old man winter to try and make your hands feel cold for the next few months.