This article is from the Bicycles FAQ, by Mike Iglesias with numerous contributions by others.
Starting at the bottom, on my feet I wear Sorell Caribou
boots. These are huge ugly things, but they keep my feet
warm. I have found that in extreme to insane cold, my toes
get cold otherwise. These boots do not make it easy to ride,
but they do keep me warm (see rule 2, brute force). They do
not fit into any toe-clips that I have seen. I used to wear
lighter things for less cold weather, but I found judging
the weather to be a pain. If its not too cold, I ride with
them half unlaced. The colder it gets, the more I lace
them, and finally, I'll tie them.
Fortunately, wet days are not too cold, and cold days are
not wet. When its dry, I wear a pair of cycling shorts, and
one or two (depending on temp and wind) cotton sweat pants
covering that. I know about lycra and polypro (and use them
for skiing), but these things are destroyed by road-dirt,
slush and mud.(see rule 1 above). I save my good clothes
for x-country skiing.
An important clothing item in extreme to insane cold, is a
third sock. You put it in your pants. No, not to increase
the bulge to impress the girls, but for insulation.
Although several months after it happens it may be funny,
when it does happens, frostbite on the penis is not funny.
I speak from experience! Twice, no less! I have no idea
of what to recommend to women in this section.
Next in line, I wear a polypro shirt, covered by a wool
sweater, covered by a 'ski-jacket' (a real ugly one with a
stripe up the back. The ski jacket protects the rest of my
clothes, and I can regulate my temperature with the zipper
I usually take a scarf with me. For years I have had a fear
that the scarf would get caught in the spokes, and I'd be
strangled in the middle of the street, but it has not yet
happened. When the temp is extreme or colder, I like
keeping my neck warm. I have one small problem. Sometimes
the moisture in my breath will cause the scarf to freeze to
On my hands, I wear wool mittens when its not too cold, and
when it gets really cold, I wear my cross-country skiing
gloves (swix) with wool mittens covering them. Hands sweat
in certain areas (at least mine do), and I like watching the
frost form on the outside of the mittens. By looking at the
frost, I can tell which muscles are working. I am amused by
things like this.
On my head, I wear a toque (Ski-hat?) covered by a bicycle
helmet. I don't wear one of those full face masks because I
haven't yet been able to find one that fits well with eye
glasses. In extreme to insane cold, my forehead will often
get quite cold, and I have to keep pulling my hat down. The
bottoms of my ears sometimes stick out from my hat, and
they're always getting frostbitten. This year, I'm thinking
of trying my son's Lifa/polypro balaclava. Its thin enough
so that it won't bother me, and I only need a bit more
protection from frostbite.
I carry my clothes for the day in a knapsack. Everything that
goes in the knapsack goes into a plastic bag. Check the plastic
bag often for leaks. A small hole near the top may let in water
which won't be able to get out. The net result is that things
get more wet than would otherwise be expected. The zippers will
eventually corrode. Even the plastic ones become useless after
a few years.