1. You have to dress for the weather.
Biking in winter is a tricky endeavor—wear too little clothing and you'll be miserable out of the gate; wear too much and your core will overheat, spawning yet more misery, compounded by sweaty clothes and damp hat hair upon arrival. I've found that a thin hoodie is plenty for temperatures as low as 40, and for even lower than that, I wear a midweight faux wool coat. I cover up my legs, on the many days that I'm wearing a skirt, with a simple pair of 5-dollar leggings. Really, you don't have to work too hard to keep most of your body comfy on a short winter ride.
But for your face and hands, quality is key. In my early days of riding in winter, I got frustrated by the way my fingers always froze no matter how fluffy my gloves were, and the way the wind ripped right through all my hats, making my ears cold and my brain dizzy.
I mostly solved the hands problem with a pair of massive insulated gloves. They work so well that I have known the backs of my hands to get sweaty on particularly energetic rides...but there are still times when my fingers go numb. And wait! There's more! Since the gloves are so bulky (I think I bought them a size too large) they impede my operation of the shift and brake levers. I had one close call a few days ago where I nearly ran into a car because the fingers of my glove got caught while reaching for the brake, and I only saved myself with some artful steering and a little luck.
For the ears problem, I can mitigate it in most weather with a simple pair of furry earmuffs. I look like a fool in them, but they work better than any knit hat I've tried, and they are much friendlier on my hairdo than a headband. When the temps are below forty, I break out the big guns: A multifunction fleece balaclava that oh-my-gosh changed my life! When I'm wearing this bad boy, I'm told I look like a ninja, or like I'm wearing a burka, but I don't care, because with it on my head, I can ride like a speed demon without even feeling a hint of breeze! The balaclava is great at keeping out the wind, but that means it's also great at keeping out oxygen, which brings me to my next point:
2. You have to ride more slowly.It's hard to breathe through a windproof layer of microfleece, and I find that I can't get enough air to keep up my usual breakneck pace when wearing my balaclava. Besides, as I've mentioned, overheating because of wearing heavy clothes while exercising is a constant issue. So I've had to learn to bike a little more slowly in winter to keep my body temperature and oxygen supply consistent. But I guess that's OK, because driving slower isn't a bad idea when there's the potential for running into ice.
Despite the ongoing challenges, I'm super-happy that I decided to step outside my comfort zone and start biking in winter. This means I save a half-hour of working out every day almost year-round! An unexpected benefit is that all this new gear makes me better equipped to tolerate all sorts of outdoor activities. Just last weekend, I went skiing against my better judgment and managed to stay warm the whole time (although my nose still ran, even in the balaclava). Plus, being a winter biker gives me added bragging rights, plain and simple.
But before I can legitimately call myself "hard core," I'm going to need to learn the secrets to biking in the rain and snow. But I will figure it out...and once I do, you'll be the first to know.