The saying that "there are no bad conditions, just bad clothing choices" holds some truth, but doing a long ride in rain and 40 degree weather may make you reconsider. In many cases, riding outside in the cold-weather months is still very possible. Modern indoor trainers and rollers are incredible tools but I’m not entirely sure if doing several consecutive months indoors each year is sustainable. I would recommend supporting your local bike shops and outdoor stores by investing in gear that fits you and your bike well and to get outside!
Stay Dry
Something that might be even more important than warmth is staying dry. Clothes lose their insulating capabilities when they get wet and a potential way to prevent this is having fenders at your disposal. Fenders will prevent the water from the road getting sprayed onto your clothes by your tires. Personally, I throw on an "ass-saver" even if there is a slight chance of rain or the roads/trails are damp. I also have a set of SKS Raceblade XL fenders that work on nearly all bikes if the roads are wet.
Not only do you need to consider your clothes getting wet from the outside, but also from the inside. Many people I ride with overdress in the winter, start pouring sweat, and end up cold because they lose the insulating effect of the clothes after they get wet. As a rule of thumb, dress in a way that you might feel a bit cold the first 10 minutes of a ride. You will warm up to a comfortable temperature after the initial exposure.
It's also smart to have a good blinky light year-round, especially when days are shorter. This makes you more visible to cars and increases your safety when riding in unpleasant conditions. I currently have a Lezyne Strip Drive Pro Rear. In addition to this, you can also touch up your bike with a bit of reflective tape for winter riding. This also adds another layer of safety in case you forget to charge your Blinky light.
Temperature and Clothing Choice
Below is an example of the general combination of clothes I use for road riding in different temperatures. These are just my preferences so it will be different for everyone, but this is a good starting point. You may also need to adjust for off-road riding which tends to be a little warmer as you generally are in more wooded areas and riding at slower speeds (i.e. far less exposed to the wind), and using your upper body slightly more.
70+: bibs and jersey
65-70: bibs and jersey, arm warmers
60-65: bibs and jersey, lightweight long sleeve jersey
55-60: bib tights (or leg warmers/bibs), jersey, lightweight long sleeve jersey, generally carry lightweight gloves, may or may not use them
50-55: bib tights, light LS base layer, long sleeve jersey, lightweight gloves, shoe covers (maybe), cycling cap
45-50: bib tights, light LS base layer, long sleeve jersey, vest, neck buff, lightweight gloves, shoe covers, cycling cap with ear covers
40-45: bib tights, light LS base layer, jacket/thermal LS, neck buff, warm gloves, wool shoe covers, cycling cap with ear covers (may need winter cycling cap)
33-40: bib tights, light LS base layer, jacket/thermal LS, vest, neck buff, warm gloves (bring two sets to swap if one pair gets sweaty/wet), winter shoe covers, winter cycling cap
Dressing for cold weather is quite personal so it might take time to get it right. Having a foldable vest or waterproof shell in your pocket/bar bag is always a good option. My peers and I often refer to this as the "oh sh!t" vest in case the weather turns or you need to stop. They really do trap in a ton of heat and can save you in a pinch. You can also wear this for a few minutes to warm up at the beginning of the ride, just peel it off before you build up too much sweat underneath it.
Below Freezing
I don't do a ton of riding outside on the road if it is less than 32 degrees- this is especially true at least for the last few years because they don't really salt/grit the roads where I’ve been based in Knoxville, TN. This means the threat of ice is far more apparent on the roads. In Cleveland, OH (where I am originally from), the roads are always doused with salt/grit and even though it does snow much, much more and is way colder than Tennessee, there is generally less chance of ice. However, it gets much trickier to dress when it is below freezing.
Outside of needing a beater bike or to be prepared to wash/treat your bike very frequently when riding with a lot of road salt and freezing temperatures, you need to be far more equipped with:
Sealing extremities- either winter boots or getting creative tucking in winter shoe covers into winter tights, making sure gloves can be ‘tucked’ into your jacket, etc.
Toe/hand warmers in between layers of gloves, or outside of shoes between shoe covers
Thermal bottles or starting with warm water/mix so your water doesn’t freeze right away
Treaded or even studded tires could be necessary if you live in an area where certain roads are untreated
Clothing Specifics
Base layers- I usually go with very thin base layers that are good at wicking moisture. They don’t necessarily need to be skin-tight to layer well which I think is a common misconception. A lot of "heat gear" or "winter gear" base layers by different companies are so thick that they feel constricting and just build up the layer of sweat so quickly that they end up making you colder. Right now, I've got some from Terramar called "Transport Base Layer Top - Long Sleeve" that are 100% polyester and very nice. Many outdoor or climbing stores have loads of options on this front.
Long sleeve jersey- I've had good luck with my bike team kits the last few years for long sleeve jerseys. We've had Pactimo, Castelli, and Eliel clothing and all have wide ranges of thicknesses. This is a good chance to go to the local bike shop and find the appropriate fit and thickness for the conditions you’ll encounter most frequently.
Jacket- Most everyone I know swears by Castelli’s Gabba/Perfetto (I believe it used to be called Gabba, now is Perfetto). In fact, many pro teams buy their riders this jacket for cold or cold/rainy conditions because it is simply better than what their team sponsor has!!! Castelli does run very small if you splurge for this one, so you may want to size up once, or even twice.
Vest- Make sure it is foldable. I have some with "open" backs, where it is mesh that is breathable that I go to more often than ones that are fully "sealed". Vests are also super useful year-round when there is a chance of rain, but not actively raining and you don't want to be stuck in the rain cape that gets super sweaty.
Bottoms- I generally wear bib tights in the winter. I find it difficult to find good fitting leg warmers that don't either bunch up or feel constricting around the knees. This might not be the same for you. Bib tights also by Castelli are pretty incredible and are good for very low temps but are also fine up to the 50's because they are made of such quality wicking material. They do run very, very small (I'm 6'1" 175lbs and wear XL, most bibs I'm L) and are quite expensive, but are also my favorite piece of clothing.
Shoe covers- I really like Defeet for dry weather. I have a pair of their Slipstreams for upper 40s to 50s, then a pair of the wool ones for upper 30s. If it is <35 or a chance of being wet, winter shoe covers might be necessary. Right now, I have Bontrager RXL softshell storm covers for truly winter conditions. I've also had good luck with Gore Wear winter shoe covers, and some of my peers like Garneau and Endura. I like the zippered softshell ones best.
Gloves- Defeet is good again for dry weather and most bike shops stock these or an equivalent for mild temperatures. I have a couple pairs of these along with my "Amazon gloves" for cold weather which are also nice and not wildly expensive like everything else I've mentioned so far (“Winter Touch Screen Warm Gloves for Cycling, Amazing Thermala Premium Thermal Windproof Gloves.”) If you truly have cold hands or Raynaud's syndrome, I’d suggest looking into Toko gloves.
Cycling caps- Like everything, there are different thicknesses and varieties. One that has a "windstopper" is nice for <45 degrees. I generally try to keep my ears covered below 50 degrees. 50-60 degrees is probably the optimal range of using a cycling cap without ears. I’ve also seen riders taping the vents of their helmets if they have a very ‘summer’ helmet, but many aero helmets are already pretty sealed off (and subsequently very hot in the summer), so this may not be necessary.
Other Clothing:
Jumbo sunglasses cover more of your face and can make you feel warmer and yellow lenses can make it feel sunny even when the weather is drab
Pre-opening snacks that won’t spill everywhere can make it a lot easier to eat without taking off gloves
Keeping your shoes/helmet inside before riding so there is no chill in them before riding is a huge advantage to not feeling frozen at the start of the ride
East/west roads can get more sun and dry faster, but subsequently have more sun glare (ride with a blinky!)
Carry a bonus pair of gloves in case the initial pair gets wet from rain, snow or sweat. Wet gloves lose their insulating capabilities.
Coming prepared with at least 1 tube, a good hand pump, a multi-tool, a charged phone, and a key to get back into your house can save you from spending a lot of time getting cold outside!
Other Tips
- Cycling requires a ton of gear to be comfortable! However, there is a LOT of overlap between temperature ranges and layering can make many conditions totally fine.
- You may need two or three options in thickness for long-sleeve jerseys/jackets. Thermal long sleeves or ones that are fleece on the inside are very good, but also very warm, so save these for particularly chilly days.
- A neck buff is very nice in temperatures <50F as it acts as another layer between you and the elements. It traps in a ton of heat, and can be pulled up to your eyes to warm up the entire face/air you breath in, and is easy to take off if you get too warm.
- Living in a hilly area in the winter is particularly difficult to dress for. Plan to unzip layers if you are climbing for more than 5 minutes, and subsequently plan to zip up if descending for more than a few minutes. If descending a mountain that will be 5 minutes of zero pedaling and running into LOTS of wind, take the 10 seconds to stop and throw on the bonus vest and gloves before you lose all that body heat.
Winter riding is not only possible, but quite enjoyable. It may require a bit more planning and preparation, but I believe it’s worth it in the long run. It’s also a great way to include a bit more variety into training instead of riding around Watopia for the millionth time on Zwift.