Photo by Jason DeVarennes

Dressing for Winter

It is often said there is no such thing as bad weather, just bad clothing.

Both Fear Rothar and I are year-round cyclists, and have been for more than 30 years. In that time, technology has evolved and we have changed a few things to take advantage, but the fundamentals really haven't changed - dress in layers, starting with a light wool (or other wicking fabric) baselayer, add additional layers as temperature dictates and top it off with a wind/waterproof jacket (prferably with with underarm pit zippers) for wet weather or additional warmth on descents. Complete the ensemble with good gloves, warm winter shoes and a proper hat. That's it. Nothing complicated. Nothing else to see here. Be on your way now.

What? Still here? You want actual details? Well this is likely more than you really ever wanted to know. But you asked for it!

A little disclaimer: In this article, I will talk in both general and specific terms. For instance I may discuss what to look for in shoes and then I may include the details for shoes that work well for me. There is no sponsorship here. If you are looking to buy stuff, start at your local outdoor or bike shop. Google, of course, is a great resource for those hard to find items, not available at your local shop. ebay and craigslist are also good places to find bargains on things didn't work for someone else. Maybe it didn't fit, or maybe they gave up and moved to somewhere warm!

Also before I get into too many details, let me emphasize that one does not have to spend a fortune on equipment and clothes for winter riding. However, I do believe that good winter gear is worth its weight in gold - whether it is 0F and snowy or 35F and rainy. My winter arsenal does include a few pricey items, most notably - my winter boots. In fact, if you are looking for the biggest bang for the buck for winter cycling comfort, I gotta say that winter boots are the place to start.


While I seek maximum ventilation in summer shoes, winter shoes should be well insulated. With that in mind, I also recommend getting a size larger in winter shoes so one can add insulation in the form of heavier socks and insulated or even heated insoles. Many people make the mistake of using the same shoes or same size shoes and trying to stuff thick socks into them in the winter. A shoe that is too tight will restrict circulation and as a result your feet will feel even colder.

The first winter boots I bought (over 20 years ago) were from Sidi. While warmer than anything I had used previously, these boots had no real insulation, so a few years later I bought some nicely insulated Lake Winter Cycling Boots. The original Sidi boots then became my early spring shoes. (Sidi has improved the winter boots over the years and newer models have more insulation.)

Then 45NRTH came along. Headquartered in Minnesota, where winters are proper, these folks are using real world experience to make some amazing winter gear (more than just shoes). After moving out to Western Mass and taking up Fat biking in the winter, I decided it was time to get serious and bought some 45NRTH boots. They make several different winter boots for mild to extreme conditions. The Ragnarok is the shoulder season boot. The Wølfgar is for the most extreme conditions. The Wölvhammer is in the middle. I got the Wölvhammer and have been thrilled. I use them for both fat biking and winter road rides. There is a brand new taller version of the Ragnarok that has been announced, but not yet seen in stores. I am planning to get these as my new shoulder season boot as I have passed my old Sidis and Lakes onto friends. 

After many years of use, I had some issues with the velcro on my Sidis no longer holding, but my friendly local cobbler replaced the worn-out velcro to give them new life. After many years of use, and many open/close cycles, I also broke a steel lace on the BOA closure on my Lakes. Fortunately, BOA has replacements. They seem to have a million different models, so you'll need to know the model and year of your shoes when getting replacements. It might actually be a good idea to just order replacements to have on standby whenever you buy shoes with a BOA!

After the bike, cycling shoes are likely the most expensive specialty items you'll need for cycling. Winter boots are no exception and you may suffer sticker shock looking at the price. But by far, winter cycling boots are the best investment I have made in my quest to stay warm and comfortable when cycling through the winter!

Boot dryers

Last year, we added a couple of new tools to the arsenal in the form of boot dryers. One is a Warm air dryer that pkugs into a wall outlet. The other is UV Santitizer that runs off USB. At this stage we likely all have USB charging stations, and adding yet another USB device is not a big deal. The USB device does a good job of drying a damp shoe, while the air dryer works well for a truly soaked shoe. Both help keep the stink factor at bay. The USB model is more compact for travel. 

Base Layers

Now now let me get back to basics... or more to the point, base layers.

One of the biggest mistakes that people make is overdressing. Exercise generates heat (and sweat). There is nothing more bone-chilling than wind blowing through damp clothing! It is as important to avoid overheating and sweating is as it is to keep the cold out. It is a true Goldilocks dilemma, but it is not impossible to find just the right balance. If I am slightly cool when I step outside for my ride, I'll likely be comfortable when riding. I'll add the caveat that it also depends on how hard you will be riding and how much climbing is involved. I can dress lighter for a spirited hammer session than for a slower casual fun ride. Also all day rides are a much different beast from a one hour sprint. And mountains present a different set of challenges altogether. Finally rain at 35F is much worse that dry and sunny at 20F. So if you are one of those folks who creates a spreadsheet of clothing based on temperature, add columns for hills, wet, casual, etc.


It is probably obvious that zippers provide a simple elegant means of temperature regulation. Tops with long or full front zippers and jackets with pit zips allow a rider to stay comfortable through a varying range of temperatures, simply by opening or closing the zippers. When shopping for a jacket, I look for pit zippers. This is a feature worth paying extra - although I think all jackets should come with them!


For me, a typical winter day starts chilly, warms up through the middle of the day, before getting cold again as the sun goes down. With multiple light layers (as opposed to a single heavier garment), you can remove clothes as you warm up and then put them back on when it gets chilly again - whether due to pure temperature changes or perceived ones.

The big secret to staying comfortable in really cold weather is riding below the sweat threshold. With some prudence in regulating effort, and using zippers to control ventilation, you should be able to achieve this goal easily in rolling terrain. You will be warmer if you are dry.

It can be harder to avoid exceeding the sweat threshold on a big climb in hillier or mountainous terrain - ah that's what she meant by perceived temperature changes. We now live in an area with big climbs out the door. Most rides involve a big climb to lunch, followed by a chilling descent. For these rides, I carry a spare baselayer. No matter how easy I may try to ride on the climb or how lightly dressed I am, I'm still likely to arrive at the café soaked in sweat. I'll quickly change into my dry top before sitting down to enjoy a hot meal. Then I'll add a windproof jacket (or lightweight down puffy) for the descent. We refer to this as Elmer's Rule. Elmer's is the café we reach after climbing 2000 feet from home. It's downhill the whole way back!

Exercising in cold weather is very different from just standing around outside, like waiting for the bus or watching a football game. When exercising, you are generating heat and it's really important to use fabrics designed to wick moisture (sweat) away from the body.

Cotton is not a wicking fabric. Once wet, it stays wet! So save all those free cotton t-shirts you get on centuries for something else. And forget about that cotton sweatshirt too.

Wool is one of the best choices for a base layer. It is warm in cool weather and can also be surprisingly comfortable in warmer conditions. It's also one of the best fabrics to wear in rainy conditions, since it will keep one warm even when wet. Unfortunately, in the old days, most wool cycling apparel was quite itchy and many cyclists, myself included, moved to synthetics. But synthetics have a bad reputation for getting stinky and retaining odor - even after washing.

Fortunately merino wool is a miracle fabric! Merino wool fibers are much finer and therefore less itchy than your grandpa's wool. I wear merino wool right next to my skin with no problems. And I can wear the same top for a week or more on a bike tour without washing it and without it smelling like a toxic waste dump. It simply does not retain odor like synthetics. Merino wool is now the staple of my wardrobe - both on and off the bike.

Now for those with wool sensitivities who are still looking for a natural fabric, silk also has nice insulating properties and works well as a base layer. Silk also packs small and light, and therefore works well for multi-day tours. It can be harder to find simple silk baselayers, but I've had good luck at outdoor shops like REI.

Finally, base layers need not be cycling specific. It's amazing how much rear pockets (or trendy logos) add to the price of a garment!  Smartwool make some nice zipped wool t-necks, which work quite well as a base layer. They also make nice wool socks. New Zealand, home of 44 million sheep and 4 million people, is also home to several makers of high quality merino wool clothing, including Icebreaker. This list could go on...That's what Google is for.

Today, thanks to the comfort and versatility of merino wool, it has become very popular choice for cycling specific tops, i.e. those with pockets in the back! There are so many companies making wool jerseys and other wool cycling apparel that I'll leave this as an exercise to the reader with a google search.

As mentioned previously, the most appealing aspect of wool is that it is odor resistant. Wool can be worn many times between washings without getting stinky. I usually just hang my wool sweaters and jerseys to air out and only wash them when they are actually soiled, or if they do start to smell. The one caveat is when you finally do need to wash it, wool does take a little extra care versus synthetics.


Detergents strip wool fibers and cause wool garments to full - puff up and get fuzzy. There are many well known detergents that claim to be good for wool. Don't fall for it. They may be less harsh than standard detergents, but are still not the best for keeping your woolies looking good.

We use Kookaburra Wool Wash. It really is designed to protect wool fibers. It also doesn't need to be rinsed out, a process that can also damage wool due to differences in wash and rinse temperatures. At home, we have a front loading washing machine that has a much more gentle spin than a standard top loader. According to Kookaburra's recommendations, we just run the rinse cycle putting the wool wash in the fabric softener dispenser. When touring and hand-washing, the lack of rinsing also saves lots of time.

Dryers are the mortal enemy of wool! Hang your woolies on a rack or clothesline away from any heat source.

OK, enough about laundry.

Let's get back to getting dressed for that chilly ride.


I start out with shorts, a wool crop top, and a long sleeve lightweight wool top. A tip for the frugal cyclist: Since I'm most likely adding tights or pants, I have a special drawer where I keep my winter shorts. These are the ones that are too worn out in the back to wear without embarrassment, but are fine under another layer. I have marked the tags with a big red X!

More layers - legs

Arm, knee and leg warmers are great for those rides that start out cool, but warm up enough to expose some flesh. Warmers are easy to push down or pull off on the move. They tend to be pretty compact so can be stored in a pocket or seat bag when not in use. I have both lycra and wool versions of various warmers for different temperature ranges.

Tights, being both more complicated to remove on the move and taking up a bit more space when stored, tend to work better for a ride with a fairly constant temperature, or where the temperature doesn't rise enough to justify removal.

I prefer tights without a chamois, so I can wear them (over shorts) multiple times between washings. (Note that I use fenders, so I'm not getting spray up the back of my tights).  

I have had a love/hate relationship with bib tights for a long time now. I don't seem to be proportioned like designers expect female cyclists to be, and sometimes struggle with shorts slipping down, so bibs are great for me in that respect. But then there is the hassle of taking stuff off when stopping for a pee break. Luckily for me (and other female cyclists) Velocio created a design to address the pee break issue with their fly bib tights and bib shorts. The fly bibs are designed to make bathroom breaks for ladies possible without having to remove jerseys or jackets. The cut is low in the back, with a flexy panel to make pulling them down possible without removing a top. But the fit is secure/snug enough to avoid a draft up the back, making them a good cool weather choice.

I also have some well loved and well used windproof pants from Sporthill. A search for Nordic Ski pants will return a variety of similar options.

If it's cool and wet, I prefer to keep my shorts/legs dry, especially for a long ride. I have some Paclite pants from Gore that do a great job. These are also really nice for commuting into work in the rain, when it's handy not to arrive soaked.

For more extreme conditions, either bitter cold, or very wet, I have a pair of insulated waterproof pants from Showers Pass. It seems that people who live and ride in the Pacific Northwest know a bit about dressing for cold and wet. And of course 45 NRTH have some nice looking softshell pants as well, although I have not used them.

As the temperature goes down, I go with multiple layers on my legs. I will use long socks and knee warmers under tights and/or softshell pants.

More layers - upper body

As a petite woman with skinny arms, I have a tough time finding arm warmers that will stay up. I have some size small arm warmers that I can only use as a second layer, since they simply won't stay up! The only arm warmers I have found that will stay up on my bare arms are made by Rapha.

A wind-vest is invaluable for varying conditions or to put on before a descent. Vests are handy when a jacket is too much, and are more compact than a jacket for stuffing in a pocket. There are loads of different models out there, some lighter or heavier than others, with and without pockets and different levels of visibility. My current most used vest is high-viz orange and has pockets. While I'm of the opinion that drivers only see what they are looking for, regardless of hi-viz colors, I tend to go for the brighter colors in the winter, especially since it's so easy to get caught out in the shorter daylight.

I have a couple of outer layer/jackets. As I mentioned above, I place great value in pit zippers, so I will spend a bit more to get a jacket with this feature.

One of my most used and most versatile winter cycling garments is my Rapha Ladies winter softshell. It has two large rear pockets, plus a third smaller one in the middle. The middle pocket has been handy for storing a vest, although I believe it's intended for a pump. The waterproof zippered pocket is handy for things that need to stay dry, but not necessarily immediately accessible, like maybe an electronic car key. I often have my camera or phone in the other pockets for quick access. The softshell fabric provides insulation, protection from the wind and is somewhat water-resistant, while still being soft and comfortable. The large pit vents make it easy to regulate temperature as conditions vary. It has a fold away bum flap that can help with some amount of road spray should one be fender-free (although that never happens to me). The bum-flap also has a big reflective logo, useful when caught out at dusk or later. I have stayed comfortable in conditions ranging from 20F up to 50F, mainly by varying the weight of my chosen base-layer. I also carry a lightweight rain shell to supplement on chilly descents or in case of rain.

Rapha now also offer a hardshell waterproof version of this jacket, eliminating the need to carry a separate rain jacket for more extreme conditions. The bright colors are appealing and it has loads of reflective piping, so it is well suited for lower visibility conditions of winter.

No matter what the forecast, I always carry a rain jacket in the winter. My current favorite is a Gore Shakedry jacket. It is truly waterproof and packs super small, so I always have it with me. The one thing you can definitively say about New England weather is that it can be unpredictable. It isn't so much that it is constantly changeable or that the forecast is never right. It's just that sometimes it is wrong and frankly, I don't ever want to be caught in a 35 degree rainstorm without protection! The coldest cold you'll ever experience is rainy 35 F without rain gear, far more miserable than dry -5 F.

Hands, Feet and Head

Sometimes people miss the obvious when facing issues with cold extremities (hands and feet)

  • Protect the brain!

    The brain protects itself first. Extremities are the lowest priorities. So the most important item of clothing for keeping the hands and feet warm is actually what is on your head!

  • and Insulate the pipes.

    It really should be obvious that the hands and feet are at the end of your arms and legs, and the warm blood you'd like to have flowing around your hands and feet has to pass from your heart inside your nice warm core out through the arms and legs to get to the hands and feet. Imagine your hot water heater working away down in your basement, but with un-insulated pipes running outside the house to get upstairs to your shower, or the duct work from your furnace running outside the house before reaching a vent in your living room. A lot of heat will be lost through those un-insulated exposed pipes and ducts. 

    I am always amazed when I hear someone who is wearing shorts or knee warmers (i.e. knees or shins are bare) and overshoes, complain about their cold feet. The rider will often say, "But my legs aren't cold, it's just my feet." Remember the blood that warms the feet has to travel through those exposed legs to get there. So be sure that you have enough insulation on your arms and legs. You may have the warmest gloves ever made and still have cold hands if your arms aren't adequately covered.

Hats and headbands

I'm not your mom, but I really can't emphasize enough how important it is to keep your head covered. The body protects what it considers vital first, so if your brain isn't warm, heat is diverted from the extremities to protect the control center/brain. This is why it is often said, "If your feet are cold, put on a hat."

I use a wool headband for mild temperatures, a wool hat for cold, and a wind-stopper skullcap for bitter cold. Hats need not be cycling specific, although I do have a nice peaked cap with ear flaps that is.

I have both wool and fleece neck warmers. These are one of the best and yet most overlooked pieces of winter cycling gear. Even the best jackets won't completely snug up around the neck, allowing cold air to funnel in. A long neck warmer can also serve double duty as a face mask.

A helmet cover designed to block the wind coming through those (wonderful in the summer) air vents is also helpful.

In extreme conditions, I have even been known to use ski goggles. These are really reserved for temps below 5F. Anything above that and they are just too warm for me. They eliminate issues with glasses fogging up when stopped at traffic lights, and keep the eyeballs from freezing!


Glove liners are essential for me. I always have a pair with me. They can add several degrees of comfort to any glove, extending the range of the outer glove significantly. They are also great with big bulky gloves for when you need to take the outer layer off, to operate a camera or open an energy bar for instance.

I have more than half a dozen pairs of gloves for winter, each for a specific range of temperatures. John claims I can feel the difference in 1degree Fahrenheit. I'm really not that sensitive, but I do have different gloves for <20F, 20-35F, 35-50F and 50F+

Although sometimes I'll misjudge, since it's not just temperature that affects how my hands feel. So I've learned to carry a second pair of warmer-than-I-think-I-might-need gloves with me just in case.

The gloves pictured above from Chiba are labeled waterproof. Waterproof is a real challenge for a glove - and is somewhat dependent on the design of the jacket. If the sleeve is snug at the wrist and the glove fits outside the sleeve, water will get inside the glove due to capillary action. Despite my preference for loose sleeves with a Velcro closure, so it can overlap on the outside of the glove, sadly most jackets are not made this way. I have used these gloves commuting in 40F rainy conditions. They have cycling specific padding and grips, and the very important terry cloth thumb for wiping runny noses. They have a warm fleecy interior, but are not so bulky that they would cause issues with integrated shifters. I've found these gloves at a shop in the US a few years back, but they aren't very common here or easy to find. I did find this online retailer, with a massive selection of Chiba products, including electrically heated gloves!

I have added Lightweights reflective dots to many of my gloves for added visibility at night. I used the fabric specific version and ironed them on. The dots have survived many washings.

As it gets below freezing, it is less likely that one has to worry about hands getting wet from rain! My next warmer gloves are a pair of well insulated ski gloves to which I've also added some reflective tape from lightweights. These have enough room to supplement with a light glove liner, and/or a padded cycling glove. I'll also point out the security cords on these - very handy if I need to pull the gloves off on the move to take selfies and other photos!

Mittens are much better than gloves for keeping hands warm. With gloves, there is a greater surface area exposed to the cold, and every finger is isolated. The disadvantage of mittens is some amount of lost dexterity. Since I mostly ride fixed gear in the winter or use bar end shifters when I do ride a shifty bike, it's less of an issue for me. I have a few pairs of mittens for different temperature ranges.

My ultimate mittens are a pair I got with my Lake boots years ago. Naturally, they are no longer available! They have a nice warm fleecy lining, and a heavy canvas outer. They are roomy enough to use with a moderately thick glove liner. And they have a little zippered pocket for one of those disposable hand warmers. They have some reflective material on the sides, which faces back when my hands are on the hoods. These are good for temps below 25F. I've used these many times in single digit temperatures.

I have a whole new fleet of light to midweight gloves from Sporthill, makers of great gear for cross country skiing. 

And finally, I will also mention handlebar mitts like Pogies (Revelate and 45 NRTH), Moose Mitts and Bar-Mitts. These are oversize mitts that attach to the handlebars at the brake levers. Most are designed for flat bars, but there are some are made for drop bars. The idea is you wear a lighter glove or glove liner and place your gloved hand inside this mitt attached to the handlebar, which provides ample insulation while leaving you with fine finger control for brakes and shifting.

So back to where we started with the feet...

I use wool socks year round. I have a variety of long and short (thick and thin) socks from Swiftwick, Defeet, Smartwool and Bridgedale. There is nothing cycling specific about socks for me, but I admit to recently getting some deep winter socks from Rapha, when I was looking for a knee high sock to use with knee warmers under my tights to make a full additional layer on my legs. They have added windproof material to the toe and front of the sock. The price was comparable to various socks marketed for skiing.

The biggest issue with heavy socks is having room for them in your shoes. I talked about shoes at the start of the article - if you can remember that far back! Winter shoes should be a 1/2 or more size larger to allow for heavier socks, as well as room for those disposable toe warmers, or electric insoles. Winter shoes should be insulated, not ventilated, and heavier models will likely keep your feet warmer that super-light ones.

I use recessed cleat walkable shoes year round, but definitely recommend walkable shoes for winter riding. There is nothing worse than putting your foot down on an icy surface and falling down because the cleat slid on ice!


I rarely need an additional layer with my winter boots, but for lighter shoes or really wet conditions, an overshoe can extend the comfort range. Fenders and long mudflaps are even more helpful for keeping feet dry.

I mentioned earlier that I good winter boots will last forever. I can't same the same for overshoes. I have to replace them every year. I've been searching for years for overshoes that will last multiple seasons. Most have flimsy soles that wear out quickly if walked on, but I have found a few in my travels with thick rubber soles - which hold up much better. Of course the downside is that they are bulky and take up a lot of space when stored, which is a consideration for touring more than winter rides. I have some flimsy lightweight packable shoe covers for tours, and keep the bulkier ones for occasions where stowing them is not an issue.

My favorite overshoe (that I used for years of commuting) is no longer made. It had a good rubber sole with a cutout for the heel and the cleat, and a Velcro closure in the rear to make it easy to get on and off and adjust for different size shoes. I really like not having a zipper to get clogged with mud. The lesson for me is when I find something I like, buy a spare or two, since they may no longer be available when I need new ones!

I avoid neoprene totally. Every time I have tried it, I just end up sweaty, wet and cold. Some people tell me it works well for shorter rides, but I have had no luck with it, and avoid it completely. Given how much of it I see in shops, it must work for some folks - I'm just not one of them. I prefer overshoes made with Goretex or Windstopper.

But even heavy winter boots and overshoes aren't always enough. Sometime it gets downright cold! There are various types of hand and toe warmers available. For the price of a cappuccino, one can get disposable toe or hand warmers. They last about 5 hours and are terrific. I keep a couple of spare packs of toe warmers in my saddlebag throughout the winter for emergencies. I have given them away often.

Years ago I had electric toe warmers from Hotronics. I used them lots and eventually wore out the rechargeable batteries. A while back, Fear Rothar broke down and got a new set. He doesn't leave home without them these days!


OK. Fenders aren't clothing, but they will keep you and your clothing and your feet cleaner and dryer (and therefore warmer). There's more info on how to outfit your bike for winter here...

So congrats for making it to the end. Now let's be warm out there!

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