My co-worker Kelly was just getting into bike commuting when she became pregnant with her first child. Charlie (It’s short for Charlotte) was born and a new way of life came with her. Now that Charlie has settled in at day car, Kelly is looking to get back to bike commuting. She plans to start on Wednesday.

Today she took her new hybrid bike out with disc brakes (a major upgrade) for a trial ride. Despite temperatures in the high 40s and low 50s, she froze. So she wants to know what to wear.
It depends. Here’s some advice. YMMV.
Kelly rides about 7 or 8 miles to and from work and has only one hill (the abrupt climb to the intersection of doom). The last five miles are along the river, exposed to the wind.
Here are the rules. There will be a test.
Fashion is optional. If you are rocking the fashion world and freezing your ass off, you have more vanity than common sense. You are pathetic. You deserve your suffering. Quit bike commuting and take up Buddhism. Unless you are Coffeeneur or Ultrarunnergirl. They manage to pull off style and comfort with aplomb.
Wear layers. Your first layer is a shirt made of a fabric that wicks sweat away from your skin. No cotton against the skin. Next you need an insulating layer. For temperatures below 45 degrees I wear an old wool sweater over a short sleeve base layer. Above 45 degrees I wear a long sleeve base layer with an oversized t-shirt on top. On top of that I wear a waterproof shell. Pit vents are good. (They are zippered openings under your arms to adjust you core temperature. A zippered front is good too. My shell has a flap over the zipper to reduce air penetration. When it’s a little warmer and dry, I switch to a vest. Some of my #bikedc friends have wool cycling jerseys. They have more money than you.
Break wind. Except when there are cyclists or runners behind you. I kid. Cyclists generate their own wind. To add to the problem winter means higher winds. Your ride from the airport to Rosslyn along the river can be brutal. You’ve already got your torso covered. When it’s under 60 degrees, cover your legs with a wind proof layer. (Water proof is even more better.) You don’t have to wear much underneath. A pair of bike shorts or just wicking underwear will do most days. When it’s cold, layer. Frozen noo noos are no fun fun.
Prepare for two commutes. Become obsessed with the weather. Choose you clothes for the weather in the morning and in the evening. For me that means, I might swap my wool sweater (morning) for my undershirt (evening).
Cover your head. This is very personal. I have a hood on my jacket, a winter skating cap (without the goofy ball on top) and a buff. Buffs are the best. They can be used for all kinds of head covering. If it’s below freezing consider wearing a balaclava. Do not wear a balalaika or a baklava. Just don’t. I have a balaclava but I don’t wear it very often. I think my system of three layers works better for our DC-area climate, because it’s flexible.
Extremities are hard. I think bike-specific winter gloves are worthless. Except for lobster gloves. These are the spork of bicycle clothing. They have three finger slots: thumb, index and tall man, ring and pinkie. Think skiing! Better yet, think mittens. I have a pair of mittens made of Thermalite. They are comfortable below freezing and block the wind well. On super cold mornings, I throw chemical hand warmers in them. For your feet, wool socks are a must. On super cold mornings I wear a pair that covers my calves. Don’t wear two pair. You want air circulating around your toes. For cold wet mornings I wear Gore Tex hiking boots. (I don’t have clipless pedals.) For cold dry days, I put cycling boots over my mountain bike shoes. (Buy the boots one size too big.) If it’s going to be super cold, throw some hand warmers in your shoes. After twenty years of winter bike commuting, I still don’t have foot comfort figured out. So…
Experiment. These are things that work for me. You should try wearing some of your hiking and skiing technical gear.
Some other advice. Become a weather watcher. Note which way the wind is blowing for both your morning and evening commutes. Remember that DC weatherpeople are really into hyping bad weather. Most of the bad weather misses DC. Except for the occasional flood. Kelly already has flood experience. Consider a compact inflatable kayak for those nasty monsoon days. Don’t wear a scarf, It can come loose and get stuck in your front wheel. This does not end well.
Finally, if you are comfortable walking out the door, you are over dressed. Bank on it. Don’t wear what’s in the picture.
There you have it. Now get riding!