There are some basics when it comes to dressing for the weather. If you ask 10 different people, you will get 10 different answers, mostly because every one suffers cold in different ways. One person may not mind being a little cold to have the freedom to move more while another may not be able to set foot outside when it is below 60 without looking like the Michelin Man. Rather than claim that this is the only way to approach the cold, I am going to catalog the layering methods and particular items that have worked well for me. The biggest thing to remember is that we don't live in Canada... we live in Texas. Proofing for wind and minding breath-ability is so important. You will do better having a bunch of lighter pieces and adding layers as it gets colder. Heavy pieces will see very little use in our limited winters.
Any decent base layer will do but you get what you pay for in this department. You won't need more than two (one to wear and one to wash... or one if you are willing to toss it in the dryer daily). I am fond of this one from Craft as it is not itchy and breathes really well if it warms up. I will wear one of these for pretty much every ride all season long. Nate and I have an entire drawer dedicated to this item. http://shop.craftsports.us/190983-active-extreme-cn-m.html
Most clothing companies make these. The higher quality ones will not slip and will offer good, breathable warmth. I have some from both Panache and Castelli that work for me. I have stubby little legs so I can get my knee warmers and my socks to meet in the middle but can definitely tell a difference in warmth with more coverage on this. If you can swing both knee and leg warmers, you'll be happy. If you opt out of leg warmers, get a good pair of tights.
This is ESSENTIAL. I live and die by my wind vest. Wind is your enemy on the bike and once you get a little sweaty, being able to keep the wind from causing a chill is the difference between functional and miserable. I have a good one from Panache and an amazing one from Castelli that has a mesh back for breath-ability. It is lightweight and windproof. While that one is no longer made, there are a variety of similar offerings. This is a very light piece that adds a huge volume of warmth without overheating you.
Windproof and breathable is key here. Better if it covers your ears. You can also use a winter weight cycling cap with ear flaps from Rothera or Walz.
If your beanie or cap covers your ears, you're off the hook for this step. Otherwise, look for an ear warmer that doesn't take up a lot of space under your helmet. I don't recommend any with an internal structure (headphone style) as they are designed to be worn over the top of the head will not perform well when used with a helmet.
If you have a good beanie or ear warmer and want some protection for your neck and face, a neck warmer or balaclava can offer a lot of warmth and will warm the air you breathe, big if you have a sensitive airway. Which is right for you somewhat depends on what else you have. My preference is to have a lighter weight system and a balaclava that could be layered further. I steal my balaclava from Nate so I can't make a recommendation on brands. There have only been a handful of times in the last couple of years that I have gone full balaclava, but those days would not have been possible without it.
Okay, so don't skimp on gloves. You don't have much of an ability to layer so this is one time that you have to have multiple weights of an item. I have three types of gloves: a castelli long-fingered cross glove, a lightweight wind stopping glove by Gore, and a heavy weight winter glove from Craft. Each picks up where the other leaves off and the heavy glove is a beast. I don't wear them often but I never regret buying them. A glove liner can be added to a heavy glove as well for more warmth.
Living in TX, I have never found a heavy jacket necessary. Nate has an all-weather jersey from Castelli that covers his needs more than his jacket. I have an mid-weight LG jacket that I rarely use because it is usually too heavy and restrictive. Layers of of wind resistant fabric are so much more effective. If your other layers are on point, it's unlikely that you'll need a heavy jacket. But if you do, look for one that has good ventilation, wind and water proofing, and is nice and flexible. If you have a good wind vest, then a light windbreaker style jacket is also pretty redundant. If we had more consistent winter weather with less fluctuation, then this item would become much more essential.
THESE ARE A MUST! Cycling shoes don't offer a lot of space for thick winter socks but a non-permeable shoe cover offers a shocking amount of protection. Toe covers are a poor substitute but since my shoe covers are too big, my toe covers fit underneath for that ultra-whimp level of toe warmth.
Merino socks, wind proof socks, fleece socks... all great but make sure they are thin enough. You will eliminate their ability to warm you if they are compressed. If you need an extra bit of oompf, a thick plastic bag slid on between two layers of socks will lock in even more body heat. I don't do that unless temps drop below freezing as it will make your feet sweat like mad if it is too warm.
Windproof and fleece lined. I prefer the kind without the chamois as I tend to wear them with normal bib shorts.
I have a great short sleeve goretex jersey that when added to the arsenal makes for a versatile layer without being too much. It's great over a base layer or even by itself on those days where the wind is cold and the sun is warm. This is one of the power pieces in my collection and makes a jacket essentially redundant.
The biggest thing to remember when you are choosing your gear is that you want to be cold when you start otherwise, you are wearing too much and will overheat when you are warmed up. You want your gear to be comfortable when you are going hard, not when you first walk out the door. I usually will take a lap around the block. If I am a little cold, I roll. If I am really cold, I go back and add layers. If I am nice and comfy, I take layers off. Also consider the weather you are facing: wind out of the north on a sunny day will make wind-proofing more important than insulation. If the day is cold, overcast, and still, then you will want more warmth overall. Wind and moisture are as important as the actual temps when determining how you will feel. 38 and sunny will often feel better than 50 with rain and wind. Remember, this is all a matter of the right gear and adaptation. If you don't let yourself off the hook, the winter can be a great time to lay down a foundation for next year that will make your competition shed bitter tears.
iTRI365 Head Coach