Over at Average Joe Cyclist, Joe tells us how to dress for winter cycling, and recommends lotsa layers, writing that "the key to dressing for winter cycling is to wear layers, because cycling warms you up quickly, so you want to be able to peel off layers quickly and easily. A good approach is three layers on the top half of your body, and two on the bottom."
Joe then shows all this specialized clothing, which I suppose is fine if you are doing serious cycling all winter. But what if you are just trying to get to work? Here, I like the advice from Tom Babin, author of Frostbike: The Joy, Pain & Numbness of Winter Cycling. He knows his winter biking and is much lower key. He doesn't suggest any kind of special clothing:
I try and follow that casual approach; except for my helmet, I do not have a single article of winter bike wear that I bought specifically for cycling. My mitts and balaclava are from my snowboarding days; my yellow vest, which I just started wearing, is from Regatta Sports and I used it for rowing on dark mornings. I figure now that if I felt I should wear a yellow vest in Lake Ontario, it wouldn't hurt to wear one on Toronto streets. When I bought my new puffy jacket, I looked for one that wasn't black. I have a pair of rain pants I bought for hiking years ago and keep them in my pannier year round; they are great for sloppy days. I have a thin toque I use for running; it fits under my helmet when I do not want to wear the annoying balaclava.
If you’re reading this, you probably live in a winter city. So you should already own everything you need to ride a bike in winter (unless you are one of those people who sport ankle socks and T-shirts in February and then complains about the cold): thermal underwear, mittens, a warm hat and boots. If your snowfall gets particularly sloppy, a pair of waterproof pants is a good idea too. But don’t go crazy. Keeping warm on a bike is easy once your body starts moving. Think of it like this: dress as you would for a winter walk, and then remove one underlayer so you don’t overheat. A fat-biker once put it to me this way: “Be bold: start off cold.”
Fingers and toes always get coldest; I turn in the gloves for mitts when it gets below freezing. For my toes, I wear the same shoes as Tom Babin, a pair of Blunstones; they are waterproof and really warm, especially if you buy the winter version with the sheepskin insole. (Which actually I do not recommend because the boots are too warm in spring and fall, Tom says they are fine without the insole, he just says you should buy warm socks.)
As I have grown older I have become more conservative, wearing a helmet and vest in winter. I have powerful lights front and back; it's dark, drivers are not seeing as many cyclists and may not be as careful, they often do not have clean windshields and the roads are much narrower when the bike lanes are full of snow. It is a contradiction; I hate it when everyone insists people on bikes wear this stuff, but I just feel safer in it in winter. Perhaps if people stopped yelling at cyclists about it and blaming them when they don't, and just let cyclists do what they feel comfortable in, we would all be better off.
In her wonderful Urban Cycling Survival Guide, Yvonne Bambrick lists 12 benefits of biking through winter. My favorite is still number 1: "It makes you feel like a bad-ass to know that the cold can’t beat you." The other day, when that photo at the top was taken, I really was having second thoughts. But then I got out there and did it, was warm in a few minutes, and just felt energized and refreshed and healthy and young. You can't beat that.