A Complete Clothing Guide To Fall/Winter Riding: AKA Dress For Success By Layering

A Complete Clothing Guide To Fall/Winter Riding: AKA Dress For Success By Layering.

In order to adjust and adapt to a range of riding conditions & styles it’s important experiment on your own to find what works best for you. This overall outline should act as a general guide as you begin to approach cycling in colder and wetter conditions.

Fall is here, the temps are dropping, the days are getting shorter, & winter is approaching fast.
I’ve seen a lot of people recently asking about clothing and gear for winter riding.
Here are my opinions from my own personal experience on what works best for me when riding in cold wet conditions.
Again I stress this is what works for me and what works for me may not always work for you. Remember cycling like everything else in life is heavily based on individual comfort and personal preference.

First and foremost, my number one rule of thumb is Layering.

Layering enables you to be adaptable in order to adjust to changing environmental conditions externally as well as fluctuating body temperatures internally.

The trick to this that I have found has been utilizing *multiple light thin layers* rather than a single heavier bulky one.

A 5 degree change can make a world of difference, but bear in mind humidity levels also play a huge factor on how we interpret our surroundings. In my opinion humidity can make an environment seem much colder than it actually is. For example, 40 degrees f w/ 85% humidity feels significantly colder than even 30 degrees f with 40% humidity.

Make sure you are checking your weather reports frequently before departing for your ride, while you determine what to wear & pack. Check not only the temperatures for where you currently are but also where you’re riding to. You want to be sure to check not only the current temps, wind, precipitation %, & humidity levels, but what it will be in the future as well. Typically if you’re riding somewhere, more than 5-10 miles from your starting point you are likely to experience a change in micro climate especially if you’re in a hilly area and are going into or out of valleys, and or making a significant change in elevation of 1,000ft or more.

My typical rule of thumb being pack & plan for the coldest possible conditions. (Nobody likes being 50 miles from home suffering numbness and cold wet shivers the whole way back).

The trick here is, *and I stress this being the most important*. ALWAYS leave the house COLD. There is nothing worse than over dressing and being soaking wet from the inside out 10 minutes into a ride. Your body SHOULD be cold when you first roll out. It takes your body about 15 minutes to warm up and naturally raise its internal temperature to accurately reflect how you will actually feel during the main chunk of your ride. Your body should be cold for the first 15 minutes until you literally “warm up” after that 15 minute mark of constant sustained movement is when you will truly be able to determine weather or not you need to add or shed a layer.

It’s important to know how far, and how hard you plan on riding as distance from home & level of exertion play a key role in planning and preparing accordingly. If you’re gonna be gone for hours on end you’ll be outdoors for a long time. As long as you stay moving you’ll stay warm but if you’re exerting a moderate to hard effort you will most likely sweat even if it’s cold outside. Despite getting wet you should stay warm as long as you keep moving, because the physical act of cycling is heating your body internally. It’s when you stop moving and your heart rate drops that you will become cold. Eventually, especially on longer rides you’re gonna have to stop for a nature break, a snack break, a safety meeting, or to refill water bottles.

This is when you risk getting the chills.

In order to prevent this from happing I usually pack *Arm & Leg Warmers, a Wind Vest, Another Pair of Socks, Gloves, & An Extra Cap as well as Over Shoes* should it decide to rain or get super windy. Nobody likes numb hands & feet, or cold ears.

I usually can pack all of these items into cycling jersey pockets, a saddle bag, a handlebar bag, AND OR if you have a rack; I tend to like to wrap all the extra layers inside the largest layer and bungee cord it to the rack (this helps keep your pockets free for snacks & whatever else you normally reserve that pocket real estate for) this also helps keep your dry layers from getting sweaty.

Base layers...  I used to use one but after years of using them I found that the most common issue I would run into is almost always having a wet base layer. The thing that sucks about this is no matter how many more layers you put on over that one your base layer unfortunately is almost always gonna remain wet.

Personally, I normally always dress like its summer time and go from there by *adding extra layers accordingly* but making sure to leave enough space to breathe and ventilate excess heat.

Generally if it’s 60 degrees or above I go full summer kit almost always I.E. *Bibs/Short Sleeve Jersey* (I like Pearl Izumi or Verge) *Wicking Socks* (like like Swiftwick or DeFeet), *Fingerless Gloves* (I prefer Giro), *Cap OR Headband* (whatever is gonna keep your head warm n dry but allow your brain to breathe), *Helmet* (I only own one, it’s Giro w/ MIPPS technology to protect your brain from bouncing against the inside of your skull and causing bruising or internal bleeding in the unfortunate event of a high impact crash), *Shoes* (I love my Shimano CX7 MTB shoes, they allow me to be comfortable pedaling and even walking when off the bike because of the recessed cleat placement & added side grips. I add special Superfeet in-souls for strengthened arch support and soul stiffness, this helps improved power transfer from your leg into the crank and minimizes foot slipping within the shoes, ultimately giving you more control) and last but not least *Glasses* (something that’s not gonna fog up or get coated with salt when you sweat, Tifosi or Oakley are both great at this. A polarization in the lens will help prevent glare, light adjusting lenses or adjustable inserts will helps you adapt to changing conditions throughout the day as light levels change based on tree/cloud cover from sunrise, morning, midday, afternoon, evening, sunset, twilight/dusk & even into the night. Lastly it’s also important to consider angle of the lens based off your riding style and positioning in order to prevent wind/debris from getting in your eyes and obstructing your vision, while also allowing air to ventilate and not fog up your line of sight) I know that’s a lot of very specific information and I’ve managed to get a bit off topic here but I figured I’d go into a little more detail on my basic set up for context and then elaborate on how to adjust from there.

Now that we’ve covered the basic set up we can delve deeper into the complexities of the layering process based on your riding conditions and style of riding.

If it’s damp, drizzling or 5 degrees colder I’ll probably add arm warmers (your arms get cold because they’re not doing anything but breaking the wind) I prefer arm warmers over a long sleeve jersey because can roll them up n down, or peel on or off to vent as my body temperature, and the environment changes over time throughout the course of my ride. I’ll also likely add a wind vest, this helps to break the wind on your chest and keep your core warm while allowing you to vent excess heat from your armpits. I tend to favor a wind vest that you can zip up & down from BOTH the top AND the bottom. This gives you the ability allow extra breathability & ventilation in order to prevent your core from over heating by gradually allowing adjustable amounts of heat to be retained OR released (open it up while climbing as you heat up, zip it shut while descending when you’re subject to the cold wind at fast speeds while not internally heating yourself).

It is also very important to keep your other contact points (hands & feet, especially fingertips & toes) from getting cold and going numb. Mild discomfort is tolerable for short time periods but excessive numbness can be dangerous to your technical handling abilities on the bike especially when cornering at high speeds or climbing at steep grades. You never want to lose dexterity to where your interacting directly with the bike because then you endanger not only your safety but the safety of others on the road as well.

With that being said a good pair of over shoes & finger covered gloves is an essential investment in improving your quality of life on the bike (I personally like Pearl Izumi for the gloves as I have two different pairs for cold & even colder conditions & specialized for the overshoes). You want to buy a relatively thin pair of shoe covers mainly to block wind, and rain from getting into your shoes, this help keeping your feet warm and dry and preventing them from being cold & wet.

A pair of winter specific cycling shoes can help if you want to make the investment but if you have a pair of shoes you really like; stick with them and make other adjustments to your set up as the weather dictates.

For me, I use same shoes I normally use all year long (I also only own 1 pair). Both Swiftwick & DeFeet make great wicking wool compression socks that will ensure to keep your feet dry & warm even if they do get wet (normally the wool socks are slightly thicker, so remember to be conscious of this and not to over tighten your shoes. The fit will feel slightly different at first but don’t forget, your feet WILL swell and feel restricted as blood flow increases to your feet and legs as you ride). A nice pair of overshoes will block the wind & water from getting in; that combo will help keep your feet warm & dry. If it gets too hot & your feet can’t breathe you’ll feel them begin to suffocate and sweat excessively. The nice thing about wool is, even if this does happen you’ll still be warm. (overshoe ventilation as been one my biggest obstacles when trying to dial in my layering, what works best for you will come from experimentation and personal experience overtime, tweaking and tinkering with minor changes to your set up will most certainly help you figure out what works best for YOU).

After the ride I’ve gotten into the habit of hanging socks & over-shoes inside out near a fan (or some circulating air), propping your shoes against a wall (preferably over or near a warm vent) pulling the souls out, lifting your tongues up and stuffing with newspaper if they’re wet just to keep residual moisture accumulation from creating mold or mildew (a little baking soda will help prevent your foot gear from getting smelly). Seems like a lot but if you gotta pair of shoes you really & don’t want to invest in another, this works like a charm and allows you to adapt to a wide variety of colder weather conditions.

Getting out of the rest of your cold wet kit as soon as you finish a ride will also help improve recovery times. Nothing like a hot shower after a cold ride, just be careful to ease into it you don’t want to shock your system and cause nerve damage. I like to strip & throw on some warm dry sweats to stretch in post ride while I eat (pro tip toss them in the dryer for a minute or two before changing into them and your whole world will be a million times better).

Back to the gear.

As far as your glove choice goes, you want to choose something that’s gonna be thick enough to keep your hands & fingers warm & prevent numbness but no so thick that they’re gonna be too bulky for you be able to perform basic handling skills (gripping your handle bars, fluttering break lever sensitivity). Glove insulation thickness will also be determined by, and change with temperature variations. You never want sweaty hands from overheating because they’ll eventually get cold (and pruny) if they’re wet. I typically look for a pair of gloves with smart phone touch screen compatibility in the thumb and index fingers. That way you don’t have to take them off to snap a photo on the go, attempt to message somebody on the fly, or change the music with pruny fingers should you get sweaty (not to mention taking winter cycling gloves on and off over and over again can be a huge pain in the ass) touch screen compatibility makes a world of difference to improve overall winter cycling quality of life. 

Like I said before, my biggest point to take away from this is, don’t forget to underdress and adjust as you go.  I can’t stress enough how important it is to begin your ride cold so you don’t over heat as your body warms up.

Now that we’ve gone over arm warmers, wind vests, gloves, socks, shoes & over shoe covers.


We have knee warmers or leg warmers. I used to love leg warmers but in recent years I have taken a liking to knee warmers, the only real difference between the two is length. I like to have a small strip of leg between the bottom of the knee warmers & the top of socks/overshoe covers that is exposed directly to the air as a way to help vent and regulate expelling excess heat (this also helps my legs from feeling too constricted).

Leg warmers are great for layering and tucking over and or under socks & or over shoe covers, but for me this (layering/tucking decision) depends on moisture. Usually when it’s raining, or the road conditions are wet; despite having an overshoe covers... eventually your socks and shoes are gonna get wet, or at least slightly damp. If it’s pouring you usually can manage to keep your feet dry for an hour or two but after constant pedaling in wetter conditions no matter whatever preventive efforts you have made after a while they will fail and your feel will most likely become completely soaked and saturated.

If you have fenders normally you can manage to minimize your legs and ass/back from getting sprayed and splattered by road debris coming off the rotating tires.  However, if you choose to tuck your leg warmers into your socks the saturated socks are gonna pass the retained moisture up the leg warmer, one reason why I have become partial to tucking them over top of the over shoe or using knee warmers to create that gap. In dry conditions that are colder I like to tuck them in to keep me warm-n-cozy but again like I said before, this is a personal preference & situational judgment call based on experience riding at different temperatures with different levels of moisture.

Adjusting these layers for me normally comes when I stop at a halfway point away from home before heading back, and or when you stop for a few minute break as temps drop in the evening. My base layer (Bibs & Jersey) is usually polyester, with a percentage of lycra & spandex for compression and aerodynamics. The polyester helps to absorb sweat, dry quickly, and pull the moisture away from your body.

As it gets increasingly colder you can add another thin long sleeve windbreaker as a nice outter shell to break the direct wind. I like one with pit zips or side/back vents if it’s dry (no back vents if raining) that way you don’t over heat and find yourself wet from the inside out.

Reflective material on any or all those items is always an added bonus to help increase your visibility to others on the road as the days get shorter and the nights get longer. This increase in safety will almost always provides added peace of mind for you and your loved ones back at home while you’re out on the road.

Remember, always make sure to check the weather of where you’re going as it will most likely be different from where you start. Also, make a point to check the predicted temperature/humidity/wind/potential precipitation percentage of when you anticipate being your ending ride time, then tack on an extra hour or two and plan based on that (leaving yourself wiggle room for mechanical/rest stops). Also, weather is never gonna be 100% accurate but having a ballpark frame of reference as guideline is a good place to start.

Keeping these small easily packable lightweight layers on you in order to adjust throughout the course of your ride is essential to being able to adapt to remain comfortable, warm, and dry the entire time.

I also like to keep an extra heavier duty skull cap to change into at a halfway point. Nobody likes taking your helmet off and putting a wet cap back on. Having a dry head after a mid ride break can really change the quality of your return trip or the second half of your ride.

If you’re going on a longer ride underdress and expect to be cold until your body naturally warms up then determine your layering from there AFTER the first 15 minutes of your ride.

If you’re going on a shorter less strenuous more casual ride for a shorter distance (say commuting a few miles across town to some sort of social function) for less than 20 minutes I’d say then it’s generally appropriate to overdress in order to stay warm and comfortable since you will not be heating your body up like you would during a more serious effort ride. If not, you’ll be cold and by the time you warm up you’re already there. This way you can go on a easy cruise and stay warm without showing up sweaty and cold.

As temps get even lower down at or below freezing numbers your layers will change even more. Typically at this stage in the game you might opt for the winter bib (full leg) or long sleeve jersey first, over the leg and arm warmer options, these items usually tend to be slightly thicker & the insulation may contain a percentage of neoprene in the fabric. Thicker socks & gloves as well as a face mask (with nose vents) or neck cover (that you can wrap around your face) will all come in handy. These items are almost certain to help keep you comfortable and are worth their weight in gold for preventing windburn and minimizing face numbness. nobody likes numb cheeks, cracked lips, or cold ears (the only negative issues I’ve found with face masks have been sweaty neck or fogged glasses, having one you can adjust and vent will help prevent moisture accumulation from your breath).

In this article I have discussed a lot of general concepts that have worked for me and recommended brands that I have personally enjoyed through my own experience. Again I will stress that what works for me may not always work for you. I would also like to inform you that I am in no way shape or form sponsored by or paid to endorse any of these products or brands listed above.  Like I said, I’m just telling you what I’ve tried and what I think works best for me from my own personal experience (if you represent one of the brands or companies whose products I mentioned above and would like to get a formal endorsement from me please contact me about a review or recommendation). As far as everyone else out there reading this goes; as always, feel free to reach out and ask me anything. I am always happy to provide more in-depth feedback and delve into more specific details for what I like in order to help you create a better experience for yourself on and off the bike year round.

I hope this has helped you prepare to continue riding and logging good quality miles as we move into the cold season. Remember, don’t be a fair weather rider there’s lots of great cycling to be had all year round regardless of where you live. Research your gear, & change your perception that cycling is a summer only sport. Don’t forget, 9 times outta 10, good gear ain’t cheap & cheap gear ain’t good. If it means that much to you, make the investment, and improve your quality of life.  Trust me you won’t regret it, and neither will your bike (they’re not made to be ridden May-September).

In hindsight I also find it important to mention if you do happen to be riding in an area that typically gets a lot of snow resulting in salt and brine being present on the road; you really need to make a point to stay on top of rinsing, degreasing, & re-lubricating all components (especially the moving ones) on your bike.  This will help you to protect your investment and improve the longevity of your components by minimizing damage caused by road debris resulting from exposure to these conditions. If you really want to commit, it wouldn’t hurt to get your self a “B-Bike” or a “Bad Weather Beater” That can get dragged though the harsher seasons without the guilt of damage, should you not stay on top of your demanding winter maintenance regularly.

Lastly:  Any & all products mentioned above can be purchased locally in Louisville KY at On Your Left Cycles On Baxter Ave.  The friendly and knowledgeable staff there will be happy to help answer any & all of your questions regarding winter gear. 

Drew Echelberger