A Crash Course in Winter Cycling Gear

It’s 2011 and this year you’ve got big goals on the bike. You’re ready to get out the door and start training. So for the first time you’re going to tackle winder riding! Your friends might never believe you, but with the right gear, riding in the winter can actually be just as much fun as during the rest of the year. The roads are empty, the sky is blue, and there’s a feeling of adventure as your fancy new gear allows you to comfortably brave the elements.

Maybe you’ve already been down to the bike shop and noticed there’s a ton of gear options to get you through the winter. Some of it is stuff you didn’t even know existed and you probably have some questions. Don’t panic. Here’s my little guide to dressing for winter riding like a pro.

Winter biking gear - face mask and goggles
Even Wisconsin winters don’t stop DailyMile user Geo C. from biking to work.

The Basics
First of all there is a “Goldilocks Effect” when it comes to dressing for any winter activity. You want to be at just the right temperature. Too cold and you’re shivering. Too warm you are soaked in sweat and end up wet and shivering the moment you cool off.

But unlike running, for example, your body temperature will vary wildly over the course of a ride which makes things trickier. At one point you might be panting on a climb, then freezing on a descent. Later you might have a head wind or maybe you have to stop to change a flat. However you can dress for all these conditions if you keep some simple concepts in mind.

Your arms, legs and head need to be well insulated. Fingers and toes are the first thing to suffer when the weather drops. Most of the specialized gear you’ll initially buy will be to protect these guys since they need to be constantly warm.

But for your torso, you’re going to want to use the zippers and layers to regulate your body temperature and keep yourself warm as well as dry. You’ll unzip a little on climbs and other hard sections and zip up on colder sections when you’re not working as hard. Dressing in layers also allows you to off or add items as the temps change through the day.

bike on a snowy path

The Gear
Any serious cyclist who lives somewhere with winter conditions will have several hundred dollars worth of winter riding gear. But keep in mind they all acquired their gear over a period of several years. Chose a couple of key pieces to start with and add with time. This spreads the cost out and gives you time to figure out what gear works best for you. To start with focus on your extremities: fingers and toes, then arms and legs, and finally a nice riding jacket. You can use other gear for camping or running to fill in the gaps until you build up a whole wardrobe.

But do you really need this stuff?
Well, I started riding in the winter while in college in Wisconsin. It was seriously cold and I was seriously broke. So I tried EVERYTHING to find ways around having to buy expensive cycling gear. It’s not pretty, but it can be done (with certain essentials). At one point I survived (that’s really the best word for it) a 90 minute ride in 3 degree weather in an outfit I now wouldn’t wear with temps in the 40s. But, I will say, every time I’ve bought a REAL piece of cycling clothing I was overjoyed at the improvement in my riding comfort. So this stuff can be expensive, but it’s worth it.

My Outfit
Everyone has their own favorite outfit but for the sake of illustration let me show you what I wear when going out for 4-3 hour ride in 30 – 40 degree weather. I would adjust accordingly fordistance and temperature. Note I tend to dress on the lighter side on my core since I sweat easily and prefer being a little cooler and dry.

I’ll start with moisture wicking socks that will keep my feet dry under a pair of thick wicking hiking/camping socks.

Over that I’ll slide a pair of UnderArmor compression tights. Some people will go with a pair of bib tights, maybe something fleece lined. These are great but can be a bit pricy and I’ve never had a problem with just a pair of all-purpose tights.

Next I slip a pair of knee warmers over my tights. Knee warmers do exactly what they sound like. They look like spandex tubes; like knee pads without the pad part. These are important because the cartilage in your knee does not grow back if it gets ground down. Tight cold joints do not move smoothly and increase your risk of over-use injuries down the road. Protect your knees.

knee warmers

Next I slip on a pair of arm warmers. These look just like a pair of spandex sleeves. I prefer this to a thick jacket because it allows me to put a nice thick layer on my arms but not on my chest so I don’t get as sweaty.

arm warmers

Next I put on a wicking short sleeve or sleeveless baselayer tucked into my tights.

Now that I have a base layer of winter gear over my whole body I put on my jersey and bibs as usual. Note some people will wear their tights over their bibs because they have chafing issues with the seams in their tights but I’ve never had an issue with this.

Next I’ll put on a wind vest. The nice thing about putting a vest over a jersey is that I now have 2 zippers to play with to adjust my core temperature as well as 6 pockets to store extra gear and food. I usually roll up a long-sleeve windbreaker and tuck it into my middle jersey pocket (under my wind vest) in case I need a little extra warmth. There’s a lot of room for variation here. Some people will wear 2 Jerseys, 2 vests or 2 sets of arm warmers. Some people wear thermal jackets but they’re expensive and need to have good ventilation to keep me from soaking in sweat.

Over my cycling shoes I slip on a pair of booties. Booties are insulated wind-blocking shoe covers. This is probably the most important winder riding purchase because they are one of few things that you can’t replicate with a non-cycling specific item. Trust me, buy these first.


You lose a lot of heat through your head so a good hat is important. But if you get something too thick you won’t be able to fit it under your helmet. Be careful not to wear your helmet improperly just to fit a winter hat. Also, if you get something too thick you’re going to be pouring sweat. I found a tiny little Nike hat that worked well for me.

For my face I’ll put a touch of Vaseline on the exposed parts of my face to help with the cold windy air. A beard also helps a bit here (sorry ladies).

Lastly, my gloves. I’m a huge fan of “lobster gloves”. Lobster gloves are a pair of 5-finger gloves inside a pair of 3-finger gloves. The 3-finger design keeps your fingers close together for warmth like a pair of mittens but with more dexterity for shifting and breaking.

lobster gloves

This is how I dress, but I’m obviously biased towards the items I already own so some other items to consider are leg warmers (longer than knee warmers), winter riding shoes (insulated), balaclava (head covering that can be warn in a variety of ways), heat packets for your shoes and gloves (find them at a hardware store), thermal jackets (look for ones with good ventilation), thermal vests (ticker than a wind vest) and thermal full-length bibs.

There you go! So grab some gear, suit up, and hit the roads. You’ll have a great time now and and a great boost to your fitness in the spring!

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