If the temperature is above -10C I don't worry too much, by December I'm acclimatized well enough that exposed skin is usually comfortable above that temperature as long as I keep my core warm (especially if I'm moving). After a good jacket and toque (rhymes with "fluke"), my legs always get cold first, so I start layering sweat pants underneath oversize jeans next (I wear thick socks and heavy workboots year-round, so it's good to a few degrees below freezing. If you're a sneaker person then that would need to change, maybe get some moccasins).
Below -10C I use a fuzzy sheepskin hood, three or four layers on my legs and core, either lots of socks or some Helly Hansen arctic work boots (I bought those for cleaning off piles of pipes in the dead of winter last year, they're the first thing ever to make my feet sweat below -20) a glove (preferably mitten) on your pipe hand and your other hand in your pocket with a lighter. Lighters need to be kept warm with body heat since butane stops vaporizing around that temperature, and so do most other lighter fluids. Matches don't work well either.
That works to about -30C, at which point I would stop going outside.
But, if I had to, I use thermal underwear (those things actually work really well on your legs), up to five layers on my core (thermal, sweater, sweater, jacket, jacket), light gloves underneath my Skidoo mitts, finally a scarf (I like to avoid those because they're fiddly and restrict head movement), and my fuzzy wool hood (kind of like the Helly Hansen boots I can't remember a time that my wool hood wasn't enough http://eglifarm.com/).
I'm probably forgetting stuff but you do feel like the Michelin Man.
Also, Beards are good.
Below -10C I use a fuzzy sheepskin hood, three or four layers on my legs and core, either lots of socks or some Helly Hansen arctic work boots (I bought those for cleaning off piles of pipes in the dead of winter last year, they're the first thing ever to make my feet sweat below -20) a glove (preferably mitten) on your pipe hand and your other hand in your pocket with a lighter. Lighters need to be kept warm with body heat since butane stops vaporizing around that temperature, and so do most other lighter fluids. Matches don't work well either.
That works to about -30C, at which point I would stop going outside.
But, if I had to, I use thermal underwear (those things actually work really well on your legs), up to five layers on my core (thermal, sweater, sweater, jacket, jacket), light gloves underneath my Skidoo mitts, finally a scarf (I like to avoid those because they're fiddly and restrict head movement), and my fuzzy wool hood (kind of like the Helly Hansen boots I can't remember a time that my wool hood wasn't enough http://eglifarm.com/).
I'm probably forgetting stuff but you do feel like the Michelin Man.
Also, Beards are good.
The very first pipe I smoked was on a park bench on a snowy night in February, so perhaps that stuck to my mind. The wind is annoying (soooo many matches), and if course if it's raining I find it a bit too much. But even under falling snow, if it's not too heavy, I heartily enjoy my pipe.
