Top:
- Under Armour AllSeasonGear® Longsleeve Crew
Light Long Sleeve Sweat Shirt
Optional: Rain Jacket - I usually only wear the rain jacket if there is more than a sprinkle coming down.
The above is my regular setup for Winter Riding, if it dips below the 20 then I'll throw on a short sleeve layer between the Under Armour and Sweat Shirt. The idea is to feel a bit cold at the start, but once you are rolling things warm up quickly.
Bottom:
- Running Tights (Picked up at Target)
Regular Baggy Riding Shorts - (I like Fox Mid's, they offer lots of pockets and very comfortable)
Now if conditions are really wet then I will wear Rain Pants. When looking for Rain Pants get them a little baggy so you can wear your regular riding gear under them. If you get rain pants that feel tight they will get very unconformable and feel very confining as you ride along. Another tip is look for Rain pants with Velcro at the bottom to keep the cuffs from getting caught in the chain. Many of the bike specific rain pants come with this or you can pick up Velcro bands separately.
Shoes:
Now you can get away with riding in your summer bike shoe of choice. I have done this for many years and some tricks that worked for me to delay the extreme discomfort and painfulness of feet going numb from the wet\cold. Is to wear a warm pair of socks, smart wool socks have worked well for me. Then if conditions are wet I have wrapped my feet in a plastic shopping bag with some success. It is not a perfect solution, but the feet stay dry. Some wear shoe covers and expect that the shoe covers will be trashed at the end of the season. Many have had great success in keeping the shoes dry and the feet warm. I have also seen many have a battle trying to get clipped in with these types of covers. After a ride make sure your feet are not still numb from the cold before jumping in a hot shower you do not want to experience that kind of pain.
The ultimate Winter Shoe setup is to pickup a pair of Winter Bike Boots unless you ride flats then something equivalent. Last Winter I switched to a Shimano Winter Cycling Boots, since then my feet have never gotten wet and stay warm the entire ride. The only downfall to getting Winter Bike Boots is they are nearly $200 or more. Sometimes you can find a deal in the off season. I ran without Winter specific shoes for years, so it is not a show stopper. Just do what you can to keep your feet dry, if it is just Mud and Rain you can go a long ways. When it gets down to near snow conditions that is where it gets more difficult to keep the feet warm.
When riding in snow conditions and not running flats you will find the SPD type pedals will get packed with snow often. Making it difficult to get clipped in, keep a little stick handy to clear out the snow from time to time.
Cell Phone:
My Wallet, Keys and Cell Phone I keep in a ziplock bag to stay dry. Even if it is not raining they go in a ziplock bag you never know when it will begin to rain again. The other benefit is if they fall out of your pack it is easy to locate when you go back looking for it.

