I got my first bike as a Christmas gift from my parents my freshman year in college. We bought it from a bike shop in Newbury Park, California, near where I grew up. The sales rep was happy to help me pick out a jacket and some gloves, knowing I would be going back to New York winter in just a few weeks. Fast forward to me excitedly heading out to Central Park in January in my new jacket and gloves, plus running tights and the shoes I bought for spin class. I was not a mile into the park before I knew I had a problem. I couldn’t feel my hands. I couldn’t feel my feet. What were just “gloves” in Southern California were completely inadequate for whatever damp, windy 28 degree day I had decided to go out into. I had nothing covering my feet, and no layers below my jacket. I did one lap in the park, then put the bike under my dorm bed until April.

More than a decade later, I’ve got overflowing underbed boxes full of layers of various weights and materials. Cycling in the cold can be wonderful, but knowing how to dress for the day is a real skill, and can be the difference between your bike being a ticket out of seasonal depression and your bike being hung up until April.

A few basic tenets of layering on the bike:

Core is most important. It’s where all the most vital stuff happens in your body, and it will need the most layers.
Think about hands and arms next. Gloves and long sleeves are helpful even on days when it is nice enough to go bare legs. Gloves, as I learned the hard way, come in lots of different forms, and what works at 55 degrees will not be adequate at 35.
Knees, then feet. There are all sorts of different options for covering your legs we’ll get into below, but covering your knees when it starts getting chilly is as much about joint protection as comfort. Your feet will be the first things to go numb, but shoe covers are absolutely the most annoying piece of cold-weather cycling kit there is. It’s a tradeoff.
The colder it gets the more you need to think about ventilation. Overdressing can be as uncomfortable as underdressing. You end up sweating a lot, which then cools off but is stuck under too many layers to evaporate. Overdressing, especially on a long ride with, say, a mid-ride coffee stop, can turn you into a human popsicle.
The temperature is not the only thing to think about. Humdity, wind, and cloud cover matter, too. Wet weather requires more layers and different materials than dry, sunny days, even at the same temperatures. Your weather app’s “feels like” temperature is your friend, as is the seemingly obvious but not always practiced “looking out the window or going outside before you get dressed” method of ascertaining the weather.
Type of riding matters, too. The faster you’re going the more wind chill there is in the cold, so road bikes require more layers than mountain bikes or commuting. If you are riding a road bike, what’s the ride going to be like? Will there be a big temperature fluctuation throughout the day? Is there a planned ride stop?
In the winter, you will need 20 minutes to get dressed in all of these layers. Anticipate it. Don’t be late to your group ride and make people wait for you because you didn’t know it would take five whole minutes to get your shoe covers on, it’s cold out!
Finally, take all the advice below as a starting point. Everybody’s different — some people run hot, some people run cold, some people have various parts of their body they like to cover or don’t at higher or lower temperatures based totally on personal preference. Try some things out. No one gets it right every time, but this is a place to start with how to think about dressing for the weather as it starts getting colder. I’ve learned a lot in the decade-plus since that first winter ride I did, but I went out to Prospect Park completely underdressed yesterday and my toes went numb. It happens. Happy riding!

The Unlimited bibs are a thicker fabric that seem a little heavy in the summer but are perfect for fall.

60-70 degrees

Between 60 and 70 degrees, layers are a “maybe” for me. If it’s wet, a vest, possibly arm warmers, and thin gloves seem right. However, if it’s dry and not too windy, I’ll often go out in just a jersey and bibs, maybe with something like the Aria Vest in my pocket. Between October and April I rarely ride without a light vest either on or in my pocket. It’s a great, versatile piece of kit that folds up into almost nothing, which often makes the difference between uncomfortable and just right.

In this range I usually don’t wear gloves. I find short fingered gloves never fit me right and usually are painful between my fingers. If it is just chilly enough to want something on my hands, I usually go with a light long-fingered glove designed for off-road riding like the Unlimited glove: breathable but with grip on the inside so I don’t feel like my hands are slipping off my bars.

At this temperature range I usually don’t cover my legs because I run hot, but I also know plenty of people who think this is respectable knee warmer weather. If you have any sort of knee problems, this is the time to start considering covering them to keep your joints warm.

Photo Rhetoric - To Be Determined - Westchester Gravel Riding-2045.jpg

45-60 degrees

This is probably my favorite temperature range for riding bikes. It’s cool enough to need layers, but nothing too heavy or bulky. I’m a huge fan of a lighter long sleeved jerseys in these conditions. A regular jersey, arm warmers, and a vest works, too, and is probably more versatile on days when the temperature fluctuates a lot over the course of your ride. But I hate arm warmers, I don’t like the stickyness, or how tight they feel around my arms. I hate pulling them on and off, especially when I’m wearing a watch. I am annoyed by the seam. I’d rather pull on a thermal long sleeve jersey over a regular jersey and call it a day. (Note! The regular jersey underneath is important for ventilation! It will wick sweat, and allows you to pull the zipper down on your other layers for ventilation if you start overheating.)

If it’s wet at these temperatures, I’ll often go for something like a water repellant vest, something like the Perfetto Ros, rather than a full jacket. Plenty of people like rain jackets, but I find most of them tend to repel water on the outside, but trap sweat on the inside, and nobody likes to be clammy. No thank you.

Also consider a pair of gloves that has some water-repellancy. There are some neoprene gloves out there that are great for really rainy days, but I tend to like something that is more of a windproof/water-repellant mix for most of the time. They aren’t the best in a downpour, but they tend to be warmer on dry days, and you’ll get more use out of them. A light-to-mid-weight glove is going to be your favorite piece of gear in both the spring and the fall.

On your feet, I like to wear wool socks and, maybe at the low end of this temp range, toe or shoe covers. Toe and shoe covers are one of the most annoying pieces of cold weather gear, but it’s definitely the temperature range where you’ll want to think about how to keep your toes warm.

On my head, I’ll usually wear a sports headband that is wide enough to cover my ears. As a general rule, I like to keep my ears warm, but otherwise allow a lot of the heat I’m generating while riding out my head. I have a variety of headbands, and usually don’t put on a hat until it’s down below 30 degrees.

Because it’s Covid, also consider a neck gaiter, which keeps your neck toasty and can be pulled up to cover the nose and mouth. Above 45 degrees I’d go with a regular spandex one rather than a thermal one. I am not one to abide a sweaty neck.

Lucia in the Castelli Transparente jersey.

32-45 degrees

This is also fine weather to ride a bike in! At this temperature you’ll want to cover your whole body, but really consider ventilation. This is the zone where overdressing and overheating start to come into play. I like a base layer, a jersey, a long sleeve jersey, and a vest up top. If you run cold, maybe also some arm warmers or swap the long sleeve jersey for a jacket. Ideally, you should be a little bit chilly for the first 5-10 minutes of your ride until your effort heats you up. If you’re warm when you walk out the door, you’re likely to overheat once you get moving. (I did not heed my own advice this past weekend, rolled out of the parking lot feeling nice and toasty, and was a sweaty mess stopping my whole group to peel off several layers 20 minutes later.)

You can wear leg warmers, but I prefer tights, especially as it gets down closer to freezing. Unless you have thermal bib shorts, which are fleece-lined (a treat I do not own but wish I did), the patch of skin on your upper thighs that is barely covered by your bibs or shorts will get cold and red and irritated. You won’t feel it so much when you’re riding, but your after-ride shower will reveal angry red patches on your legs. I prefer to just wear tights. A wind/waterproof tight like the Nano Flex Pro 2 is worth the splurge if you’re already going for it, as the cold-but-above-freezing temp range is where you get a lot of wind and water on rides. Nothing worse than melting snow everywhere and a wet butt in tights that aren’t built to handle water.

That said, winter riding gear is expensive, and if you’re just starting out, especially if you’ve come from other sports, plenty of gear can be repurposed. I spent years riding through the winter in a pair of regular cycling bibs underneath (not over!!!) some fleece running tights. I’ve even ridden in bibs under yoga tights, as long as they’re the kind that are tight at the ankle. The only word of caution with this method is to watch your butt: the padding on your bibs will cause your tights to sag, and then can get caught on your saddle when you try to get on your bike after a coffee stop. Consequences range from feeling a slight tug to causing you to fall over standing still (ask me how I know).

Although there are lots of different options for this temperature range, trü heads know the correct gloves to wear when it’s 30-40 degrees out are Ninja Ice gloves, which have plenty of grip and are, at the time of writing, $9.12 on Amazon.

Consider a thermal gaiter, although as someone who runs a little hot I tend not to break out the fleece one until it hits the mid 30s. Similarly, in this range I ride in a thick thermal headband that keeps my ears toasty while, again, letting my head be my body’s vent.

You’ll want to cover your feet at this temperature, too, and I’d recommend shoe covers that are either goretex or wool, for similar reasons to why you want tights that are made to repel water.

Below freezing

Riding bikes in winter is fun! If you’re dressed properly. Below freezing is where you really want to be covered everywhere, in multiple layers, but you are really only going to figure out what is comfortable for you by testing some things out. You have to overdress and overheat and then end up freezing in your own sweat, and then underdress and be freezing from the start, to really figure out what works for you. I would say tights are a must. Shoe covers. Possibly chemical toe warmers if you don’t have good circulation. Thick, warm gloves are important. A base layer, jersey, vest, and something long sleeve and fleecy. Cover your ears. Cover your neck. Do not, however, under any circumstances, try to do both at the same time by wearing a balaclava. Unless it is under 20 degrees, it’s too hot. A sweaty head is a recipe for disaster.

For riding below freezing you’ll want a nice, thick jacket. It should be fleecy and have some water resistance, like the Perfetto RoS jacket. Time was, winter jackets like that were constructed to keep everything out and resulted in much clamminess, but more recently made cycling jackets have gotten better about ventilation. Still, a lot of jackets that will keep you really happy all day at 28 degrees are absolutely unwearable above 35. Wind chill is a bitch. The Alpha ROS will be your best friend if you’re trying to ride on a bone-chilling kind of day, but I wouldn’t recommend it above freezing.

Similarly, once it is below freezing I often break out the lobster gloves, which are halfway between five-fingered gloves and mittens. You get the warmth benefit of multiple fingers touching and heating up the same area, but still have some dexterity for shifting.

Got it yet?

As a final note, sometimes your layering needs change throughout your ride, so sometimes starting with extra layers in your pockets is the right move.

Below about 40 degrees I start thinking about bringing more layers with me than I am wearing at the start, especially for longer group rides where I might go out hard and then find myself sitting in cold sweat 30 miles from home. On a longer ride in the winter I’ll often bring an extra vest or base layer with me and put it on (or switch base layers) at the mid-ride stop. Leaving Piermont or Nyack and being just absolutely freezing with so many miles left to go is a feeling to guard against.

When I race early spring CRCA races at the crack of dawn I usually bring two full extra layers plus extra gloves, so I can completely take off what I’m wearing above the waist (sweaty!) and have a dry jersey and jacket to ride home in. Any other way is a recipe for teeth chattering all the way home (your need for this really depends on how far you live from the park I suppose).

LIkewise, I often bring two pairs of gloves with me on most winter rides. Sometimes I need a heavier pair in the morning, then switch later in the day as it warms up. Sometimes I just can’t figure out what is right and would rather have full pockets than frozen hands. If I’m doing intervals I’ll have a lighter pair to wear during the intervals when my heart rate is high and my body is making a lot of its own heat, and then a heavier pair for the warmup and the ride back home, where my hands need a little more protection.