The real key here is wind proofing. I can handle running in some pretty chilly temps, but rolling through arctic breezes at 20 mph is a whole different ballgame!
- Essentials - bootie covers (not the one in the rear). Two pairs of Smartwool socks were not enough to insulate my little tootsies against bitter winter air seeping into my shoes. A pair of decent booties did, however. Not optional! Find a pair on sale, they don't have to be fancy, just wind proof.
- Essentials - Good gloves. Again, it's all about the wind proofing. Knit gloves are NOT going to do the trick. Layers aren't great either, because you lose a little bit of control on the gears / brakes. Get some decent cycling gloves. Bonus, they are grippy where they need to be, and have a soft panel along the thumb that's perfect for wiping boogies.
- Needed, but you have some flexibility - windbreaker. This does not have to be cycling-specific, but you do need one. Also, consider layers. You don't need a heavy insulated jacket, just one that blocks the wind, and you can throw on some base layers beneath.
- Cycling pants. These suckers are not cheap - score some on sale if you can. If not, wear your cycling shorts / capris and throw a pair of long running tights over them. Some companies make knee covers...kinda like extensions for your shorts. They typically don't go all the way down, though. Go all the way down. (TWSS)
- For your noggin, a beanie or very thin headband like a Bondi band. You can also use one of those little earmuffs deals that wrap around the back of your head. Whatever you do, cover those ears....they will get COLD.
- A face cover or balaclava is a good choice, too, but don't pull it up too high on your nose. Unless you get one of those neat face masks with the little holes in front of the mouth, your breath is likely to travel right up you face and fog the heck out of your glasses. Seeing is fairly important.
