Michael Hanslip Coaching

If you want to go faster, you have to pedal harder

Dressing for Winter

If it is really cold (or really warm) then clothing selection is quite simple. When it is not so clear-cut in temperature, or the morning and evening commutes are very different, then the clothing choice becomes difficult.
I've been failing at this a lot recently. You'd think after years of choosing clothing I could get it right...
The initial shock of leaving the building into the chill wintery air should never be accommodated because as soon as the rider warms up, they'll be greatly overdressed if they worry about being warm in those initial ten minutes. And still, you don't want to get too cold. Sometimes a starting layer pays off - something that can be unzipped or even removed early in the ride.
Chill comes from the ambient air temperature, is affected by the humidity, and then there is the wind. Even on a perfectly still day, if you ride along at 30 kmh you are in a 30 kmh wind. On days like the other day, when I was riding along at 20-something kmh into a 30-something kmh headwind, then we've got some serious chill-factor to deal with.
Thus, in winter, you almost always want to be wind-proof. The waterproof breathable fabrics are all wind-proof. But they also lead to overheating pretty quickly by the amount of warm air they retain inside. (I haven't tried Gore ShakeDry fabric, but even with its excellent breathability it still retains warm air inside and therefore could lend itself to overheating.)
Wind-proof can be a single layer. This week I have been wearing a light shell jacket over the top. It keeps the wind out, but by itself would be insufficient for adequate warmth.
Accompanying the wind-proof layer needs to be an insulating layer. In cool temps that might be a long-sleeve summer jersey. In colder temps that would be a long-sleeved winter jersey. In coldest temps that would be a winter jacket.
I have two winter jackets that are also wind-proof. They're great, but if you get warm there is nowhere to go. You can't shed the whole jacket so you're stuck with the wind-proof and insulating layers together. I stopped part-way to work this morning to lose my wind-proof layer and continue with only the insulating one. Can't do that if they're one and the same.
On coldest days you might want the winter jersey under the winter jacket, but it seldom gets that cold in Canberra for me.
Extremities can get chilled pretty fast so something for the hands and feet are important. I bought some "Lobster" gloves from Pearl Izumi many years ago. I was never able to wear them in Canberra on even the coldest mornings because it has to be below -10 for me to feel comfortable in them (I got one chance to wear them in Canada on a Christmas visit at -20, where they were perfect). Lately I wear some Campagnolo brand gloves with a high-tech fabric that is water resistant and wind-proof plus insulating. And yes, they are often too hot. I used to commute in some Castelli winter gloves that were very thin - they had the wind-proof part going on but virtually nothing in terms of insulation. And that was perfect many days. No glove lasts forever and they have worn out.
On my feet, my favourite is a set of Lycra overshoes with wind-proof material at the toes. No insulation. Simply keep the wind out. That's enough for all but the coldest rides. I have some fleecy shoe covers that are also good for most rides. Because they let wind through, they aren't so good for longer cold rides - eventually the toes get cold.
One thing that never works is thick wool socks. Cycling shoes are pretty low volume. There is no space inside for a thick sock. If you do go that route, then it cuts off circulation and your feet get cold. Guaranteed.
I also tried some GoreTex shoes. They were great for keeping the rain out (as long as you didn't let it run down your ankle, because then the shoe filled up like a plastic bag and the water couldn't go anywhere). But I didn't like the actual shoe. So they got zero use for a few years and then I gave them away.
Ears can also get cold. Mostly in the commuting department I am fine. The ride is always less than 40 minutes and my ears don't get cold on most 40-minute rides. If it is frosty out, I have a thin beanie I can wear under my helmet which keeps my ears warm. It almost always has to come off after 20 minutes. I've been using the same beanie for 25+ years. It doesn't get a lot of use so it has lasted forever. I had a wind-proof ear loop (a band that goes around the head, covering the ears in the process) but it cut off a lot of hearing and ears are important on the road. It kept my ears comfortable but affected my perception of the world around me.
Once it starts to rain, then you need a different approach. The air can't be below zero, else it would be snowing. Rain means relative warmth.
Now you want water-proof. That means a membrane fabric like GoreTex, eVent or the like. Usually the water-proof layer is close to enough by itself due to the humidity (high when it is raining) and higher temps. I've often commuted wearing water-proof pants and jacket over a long-sleeved jersey (the inside of the rain jacket sleeves can be very cold when wet) and been fine.
I bought some Fox Ranger H2O pants (fully water-proof and seam sealed). I actually bought them with British Columbia in mind - there are days when I've ridden in shorts and gotten pretty wet and then cold. But with the pandemic, I haven't been to BC in 3 years and so I've used these pants for the odd wet commute. Where they've worked well. (Not sure I could ride with actual knee pads under these quite snug and non-stretchy pants anyway.)
I occasionally consider that I have too many choices. Having cycle commuted the entire time I have lived in Canberra, I have collected several winter jackets, winter jerseys, rain coats, undershirts and tights/pants. Some days I dress too warmly. Other days I never quite feel warm enough. Yet I've seen colleagues ride in the same jacket and tights from mid-Autumn until mid-Spring and endure.
Given how much their jacket stinks by Spring, I definitely prefer to be able to launder my stuff regularly and not have to try to dry it out for the next commute. Caught in the rain last week (when it wasn't supposed to rain at all) I tossed everything I was wearing in the wash on getting home and wore something else to work the next day.
Adapting clothing to temperature takes practice and an eye to how long and how hard the ride will be. If you're too warm, back off on the pedals to generate less heat. Or, if chilly, pedal harder to generate more heat. I cruise to work at about 300W. But the human body is about 25% efficient. So I'm generating about 900W of heat. That's enough to warm a bedroom. No wonder I get hot!