I must start off by apologizing for putting this post off so long. Part of me wanted to test out the recommendations and the other part of me knew a lot of the tips were in the comments section making them easily accessible. Thank you to everyone who posted a comment or emailed me. I really appreciate all the great ideas.
That being said at the very least I need to announce the winner of the contest. From the emails and comments entered I drew one winner and that is Bryan Kuhn! Congratulations Bryan! He gets a choice of a hat, scarf, or yoga socks handknit by me! Now on to what I have learned.
Get Your Mind in the Game
"The key to winter cycle commuting is just to suck it up and commit to it. If you give yourself an option, you won't do it. And, once you do it, you can't believe how easy it really is."- Brad Werntz
Many a cold and frosty morning Brad's words stuck in my mind. I could be car-free and take the bus or get a ride from someone but there is something about biking that makes my days better. My metabolism is revved, I am able to plan my day, and just be outside. It's easy in the summer, in the winter it really takes commitment. I have found prepping all my clothing and gear ahead of time makes the biggest difference. No excuses.
Remember the Outdoor Clothing Layering Basics
As with most outdoor activities, layering is the secret. I know that but I went overboard on my first winter ride. I was burning up after a few miles and stripping layers like people were throwing twenty dollar bills. Bryan's email and Technex's comment reminded me, you don't want to start off toasty. You're going to be cold at first and your bottom half doesn't need as much protection as your core. Once you get moving and warmed up you will be comfortable.
You may have heard the saying "Cotton is Rotten" when speaking of base layers. It's especially true in the winter. When choosing base layer fabrics wool or synthetics are the way to go. Recommended lines include IBEX Wool, Patagonia Capilene, and Mountain Hardwear Continuum.
I have yet to use an insulating layer on my bottom half. I just don't need it once these legs get going. For the upper body I pair my long sleeve base layer with a fleece vest. Honestly, many days I could probably go without the insulating layer, unless it gets below 35 degrees or so. However, the vest is so small and easy to throw in my bag get warm I would rather have it than not have it.
Even when it's not windy out you're going to feel the effects of wind while riding. A windproof shell makes all the difference when it comes to retaining the body heat your generating. I am currently in love with my Mountain Hardwear Mistral Jacket for milder days. It's a windproof fleece that is so incredibly soft that it's hard to believe it is windproof. It works well with just a base layer. When I am worried about getting wet I have been using my Marmot Precip Jacket to ward off wind and rain. It's fairly effective. However I have my eye on the Mountain Hardwear Transition Jacket for a waterproof and windproof layer, I have heard from friend it fits like a dream.
When the temperatures are dipping near freezing or the wind is particularly harsh you may also want to consider a windproof layer for the legs. Again, Mountain Hardwear comes to the rescue with their his and hers soft shell pants.
Head, Hands, and Feet
Let's start from the top! Make sure you noggin is protected. WHERE YOUR HELMET!!! However keeping the head warm under the helmet is important. I ordered a new helmet for winter from Bern. They make awesome multi-purpose helmets rated for snowboarding, skiing, skateboarding and cycling. What I love about these helmets are the Zip Mold Liners. They fit securely in the helmet while providing adequate ear coverage.
If you have a helmet you love consider pairing it with a low profile hat like the Mountain Hardwear Transition Dome. If you need face and neck protection consider the Buff in Merino Wool. I love my Buff and use it almost daily.
The fingers and hand are important to protect. I have found that a light liner type glove with my regular fingerless riding gloves works very well. If you need a little more protection make sure you're choosing gloves that are thin and allow for movement.
The feet! You're regular running shoes won't cut it. They freeze and aren't generally windproof. Look for windproof shoes or shoe covers. I actually wear my insulated boots most of the time or a pair of Keen trail shoes. Paired with a nice wool sock like those from Smart Wool keeps my feet at a comfortable temperature.
Keeping Your Valuables Safe and Dry
If you're going to get wet items in your bag or panniers can get wet too. Laurel Fan recommends regular Ziploc bags to keep small items dry. Great for valuable cell phones and other objects. Always take into consideration how well a bag is equipped for cold wet weather before riding with it. I use a medium size Timbuk2 bag for my day-to-day riding. It keeps most of my items dry though for precious items I pack them in a waterproof cosmetic bag for extra care.
Adapt Your Riding Techniques
Some great advice from Katie Levy, remember that when you're biking on the snow or ice small corrections are often enough. Exaggerated movements that may work well in the summer will find you slipping and sliding. Also brake softer than normal and don't lean into curves as much as you would on dry ground. There is often ice on the ground even when you can't tell it's there. Nobody wants winter road rash.
So when it all comes down to it bike commuting in winter is a personal choice. You have to have the desire, the commitment and plan ahead. It's not for everyone. From experience I can tell you it's an amazing experience especially when you're out on the road before the traffic hits. If you're going to give it a whirl please be safe.