Every year, we have to face the cold. It's a part of cycling that shouldn't be avoided because of how tough it will make you, but we have a few tricks that will make your cold weather riding a little easier.
1. Dress for the worst, but prepare for the best, AKA Layer Up! Some people I know bring two pairs of gloves when they ride. If they know it's going to get 20 degrees warmer during their ride, they may not need their abominable snowman hands halfway into the ride, so they carry a lighter pair of gloves for once it warms up. I prefer just one pair myself, but I always wear a base layer shirt, my regular jersey, and a wind jacket on top that I can easily remove and shove in my back pocket when it warms up. If you're out for a long ride and only have thick winter clothes, once the sun hits, you're going to be HOT! Remember to dress in layers so you don't end up having your own personal July underneath your jacket. For 40-50 degree rides, I'll wear arm and leg warmers that can be removed once the temperature is in the mid 50's. If it's 40 degrees or less out, I'll wear full length tights that I can handle up into the low 50 degrees without overheating. Whenever it is or will become below 45 degrees during my ride, I put on my shoe covers. My toes get cold very easily and can really make for a miserable ride when I think about them falling off.
2. Fill your tires outside, or add a few extra psi. When you subject your tires to colder air, the pressure inside the tire will drop. The simple estimate to use is 2% of pressure per 10 degrees Fahrenheit. I'm not going to subject you to the ideal gas law right now, but for you science nerds who know what it is, I'm sure you can appreciate a good estimate. If you're trying to achieve 100 psi inflation pressure during your ride, and it's 70 degrees in your house and 40 degrees outside, you'll want to add about 6 psi extra to maintain a 100psi tire during the ride. If you fill your tires outside, you likely won't see as much of a drop as you add pressure with already cold air, but the warm air inside the tire will cool and reduce the pressure. Remember, if you aren't filling your tires before each ride, you're increasing the likelihood of a pinch flat.
3. Chapstick! Do I need to explain this one? Your lips are going to freeze! Even thought I wear a balaclava when it is super cold, I usually don't put it over my mouth because it fogs up my glasses. To prevent looking like some antarctic explorer with your lips cracked, Chapstick is the bomb.
4. Cover your ears. Your ears are RUINING YOUR AERODYNAMICS! You look like Dumbo out there in the cold with your ears showing! I always wear a skull cap or balaclava under my helmet when it's cold out. Ok, it's probably not that big of a deal, but they aren't adding any watts to your ride and they're all by themselves out in the cold, so cover them thangs up!
5. Lay out your stuff the night before. I have like 300 articles of winter clothing, and my wife is ALWAYS hiding them from me! I can never seem to find my shoe covers when I need them the most. The worst way to start a ride is late, to prep your stuff ahead of time so getting dressed is easy and frustration-free. And if you can't find your shoe covers, a grocery bag over your socks will at least keep the wind from freezing your toes to death.