Winter approaches, and the icy grip of death descends from the north. The foolish cyclist hangs their bicycle on a peg and prepares for months of slothfulness in which their only exercise consists of getting up to go to the fridge; the confident cyclist, aware that even in a bad climate most days in winter the roads are clear and the only impediment to a good ride is the cold, prepares to layer up and head on out. While you don’t really need anything special to ride in the middle of February, a few well-chosen items can certainly help make it much more tolerable. Gear like this will get anyone on the road, at which point they can start letting their minds wander to the intriguing possibilities offered by generator lights.
A merino wool shirt is the single most important article of clothing for the winter cyclist. It will keep you cool when it’s warm and warm when it’s cool. (In fact, paired with a wool jersey and a shell, it will keep you comfortable well below freezing.) It not only wicks sweat away from your body, but is actually warmer when wet than when dry. Best of all, it doesn’t stink, which is nice not only because it doesn’t stink but because if you wear the same merino undershirt every day, you only have to wash it once a week, if that often (though you’ll want to hang it up at night to let it breathe). Set your space-age fabrics on fire and wear wool!
There’s no way around it: Lobster gloves look pretty stupid, even by the standards of winter cycling gear. This being true, they’re still incredibly practical. A good pair will block icy winds, bunching your fingers in pairs keeps them warm, and they’re better than bulky single-finger gloves for cycling purposes because having your fingers paired gives you more leverage on your brake levers.
No matter how well-equipped you are to ride in the cold, you’re still riding in the cold, which makes an insulated bottle that can hold some tea or coffee at drinking temperature an excellent thing to have in your water-bottle holder. Such a bottle will also hold water at the proper temperature if that’s your thing, which beats the hell out of your water freezing in a regular plastic bottle.
The heroic and fashionable cyclist goes through the whole winter with a variety of toecaps and neoprene sleeves on their shoes, struggling vainly to keep their toes from going numb. The prudent cyclist just says, “Fuck it” and goes with ridiculous-looking dual-sided pedals (they have a platform on one side and are clipless on the other), into which you can clip with your cycling shoes when the weather’s not awful (or when you’re training and need to wear your cycling shoes, questionable booties and all), but which will also allow you to wear actual warm shoes when you want to, which you generally should.
Long the top choice of terrorists, bank robbers, and goons in Jean-Claude Van Damme films, the balaclava—in merino wool, preferably—also works for the winter cyclist for the obvious reason that it keeps their entire face, head, and neck warm. (Too warm, if anything, at times, but that’s not the worst problem to have.) Not necessarily recommended for people with glasses as it can lead to fogging, which is unpleasant and unsafe, but in all other cases a fine choice.
While there are much fancier and more expensive options on the market, a cycling-specific rain jacket is probably the best choice for an outer layer for most people. The long sleeves and long back ensure that nothing will ride up and expose you to the wind while you’re leaned over on the bars, the garment keeps out the wind and precipitation while keeping in warmth, and it packs down small enough to put in your pocket. Over two wool layers, a jacket like this is all you need well below freezing, and even then you might end up pulling the zipper down to let off some heat. Buy a size up.