The biggest thing I learned when I started riding through the winter is that everything I already knew about keeping warm in the winter was useless on a bike.

Riding in winter, my biggest issue is the same as in summer--sweat management. Bundling up to "keep warm" only causes more sweat. And in winter, sweating through your clothes can be deadly due to hypothermia.

It helps if you think, not of keeping warm, but of managing heat and sweat. The idea is to remain cool enough that sweat does not become an issue. In that regard, cycling at 10°F is no different than cycling at 110°F.

You will build up heat as you ride. The trick is learning how to dissipate just enough. Dissipate too much, and you become cold. Duh. But dissipating not enough can be worse--much worse. Sweating through your layers is the first step towards hypothermia. Unless you're wearing wool (which I can't afford), your clothes rapidly lose all insulating properties when wet. The goal is to not let this happen.

The general principle is to underdress slightly, then use the heat generated by pedaling to keep warm. The standard advice is that when you step outside, you should feel a chill. If not, you're already dressed too warm.

Then, you should feel cool for the first two or three miles. If you warm up before that, you're dressed too warm.

Somewhere around three or four miles, I notice all traces of cold vanish. That's just about right for me. A few miles further on and I'll start unzipping and loosening to let a little bit of air through.

CAUTION: Since I'm underdressed, I always, always, always carry extra clothes in my trunk bag in case I flat or have some other emergency.

I also think acclimatization is key. If I want to be warm in February, I start by letting myself feel chilly in October and November. Our bodies are amazingly adaptable--if we let them do what hundreds of generations before us did.

I find, that for the way I ride, cycling-specific clothing works best. I have winter cycling boots (clipless), medium and heavyweight windfront, water-resistant tights, I use a hi-viz vented and breathable cycling jacket as my outer layer from about 45 down to zero. Under that I choose from baselayers and long-sleeve wicking t-shirts depending on the conditions. An assortment of windproof gloves, a helmet with a liner and a winter-weight cycling skullcap finishes things off.

It's amazing how little I have to wear to keep warm on a bike. And If I get cold, I just pedal harder.

About winter cycling tights

Choose unpadded bib tights, in a wind-front or windproof fabric with articulated knees.

It's cheaper to wear padded shorts since I don't have to buy seven pairs of padded tights, and it's easier since I don't need to wash tights after every ride. Plus it's another layer to keep the boys warm.

With bib tights, you don't have two sets of elastic waistbands squeezing your middle, and they stay up better. I learned both these the hard way.

Wind-front or windproof tights are the only kind I'll buy. Plain tights simply filter the breeze as it passes through. Learned that the hard way too.

When adding layers, I've found it's important to buy tights and kneewarmers that have an articulated knee. This helps maintain freedom of motion in the knees, and eliminates binding across the front, and bunching in the back.

About shoes

On the feet, there are two things to consider about your regular summer cycling shoes. First, they're designed to keep your feet cool. You have to work against their design to keep your feet warm.

Second, you probably have a nice, snug fit. This eliminates the possibility of wearing extra or thicker socks. It's the extra air space that keeps your feet warm. Compress that out, and you get cold feet. Plus, extra socks inside tight shoes compresses the blood vessels that supply heat to your feet. Double whammy.

I advise a second pair of cycling shoes for winter. I went full boat and own a set of Lake MXZ-302s. They're clipless winter boots purpose-designed for cycling well below freezing. They keep my tootsies toasty well into the single digits, before adding extra socks. They're actually too warm to wear above freezing.

You may be able to get by with a cheaper (read: less well ventilated) three-season shoe, a size or two larger to accommodate warmer socks, then booties to keep the wind and wet out. I like Endura's MT500 and new Waterproof Road booties. Think too about replacing the insoles with insulated ones (Like Toasty Feet) so the cleats don't suck heat out from the bottom.