Basic theory and recommendations for how to pick clothing appropriate to ride in year-round.
Hello! I’m Emily. I’ve been cycling more or less regularly in Chicago since around 2010. This includes Bike camping around the area, commuting through the winter, and getting around primarily by bike. I’ve also been an amateur racer since 2016 (ask me about cyclocross!). I love to overthink, optimize, and document, and I hope you might benefit from my thoughts and experiences.
The usual disclaimers: everyone’s body is different and there are a lot of variables. I’ll try to lay out the theory that works for me and you can start there and adapt to suit your needs and circumstances. This stuff is certainly easier if you have a bunch of money to spend on purpose-designed gear, but it is eminently possible through thrift stores and combinations of stuff you probably already have. Basic recommendations are based on a moderate pace 35-minute commute in the overcast daytime. If it’s sunny, it may feel a few degrees warmer; if it’s windy or dark, move to recommendations for a few degrees cooler. When it gets cold, test out your gear on shorter rides and consider your bailout plan beforehand. Your most important kit is your BRAIN: ensure you have a way to bail by taking transit or calling for a ride, with somewhere warm to wait for pickup. Bring extra layers, hand warmers, even an emergency space blanket.
| Temp range | Bottom | Top | Hands | Feet | Head/ears/eyes | Neck |
|---|---|---|---|---|---|---|
| 60°+ | Shorts | Short sleeves | Optional - you may want gloves for grip/padding | Any - prioritize ventilation above 75° & avoid black at high temps in the sun | Any - a hat with a brim can effectively protect your eyes from sun, rain, & sweat | None |
| 55°-60° | Shorts | Lightweight long sleeve | Light gloves | Any | Any | None |
| 50°-55° | Shorts | Lightweight long sleeves & opt. windbreaker vest | Light gloves | Any | Any | None |
| 45°-50° | Knickers (ensure at least knees are covered) | Mid-weight long sleeves & windbreaker vest | Mid-weight gloves | Any | Any | None |
| 40°-45° | Long pants or leggings | Mid-weight long sleeves & windbreaker vest | Mid-weight gloves | Any | Hat with ear coverings | None |
| 35°-40° | Long pants or leggings | Heavyweight long sleeves & vest or midweight long sleeves & full windbreaker | Mid-weight gloves | Any | Hat with ear coverings | None |
| 25°-35° | Wind-blocking long pants or leggings | Softshell jacket or heavyweight long sleeves & windbreaker | Warm gloves | Toe covers or boots | Hat with ear coverings | Bandana or buff |
| 15°-25° | Thermal leggings & second wind-blocking layer of pants | Heavyweight long sleeves with softshell jacket | Warm gloves | Thermal shoe covers or warm boots | Wind-blocking hat with ear coverings | Bandana or buff |
| 5°-15° | Thermal leggings & second wind-blocking layer of pants | Heavyweight long sleeves with softshell jacket | Warm gloves & hand warmers | Thermal shoe covers or warm boots and toe warmers | Wind-blocking hat with ear coverings & ski goggles | Bandana, buff or wind blocking balaclava |
| Under 5° | Ski pants/bibs | Heavyweight long sleeve top with down jacket | Pogies, hand warmers, & lightweight gloves | Warm boots and toe warmers | Wind-blocking hat with ear coverings & ski goggles | bandana & buff or wind blocking balaclava |
This is something that will prevent direct air flow from reaching layers underneath. This type of layer is important to consider since moving at bike speed essentially means it’s always “windy”. Often, a moderately effective windbreaker is the best solution. Too effective and the windbreaker can keep sweat from evaporating, but not effective enough and the wind can cut through and chill you directly. Raincoats are windbreakers but are often on the “too effective” end.
This is anything that will create a cushion of air that you can keep warm. This cushion is maintained much more effectively underneath a wind blocking layer. Fleece is great at this (sometimes too good!). Down would usually fit here but is too insulating AND too wind blocking for almost any bike applications—most people will be too hot wearing down on the bike. Cotton sweatshirts can work but be careful as they’ll make you colder if they get wet/sweaty. Merino wool sweaters are my favorite for most conditions.
I like wearing padded bib shorts. I’m heavy so I put more pressure on my sit bones and find waistbands constricting. Padded bib shorts mitigate these two concerns, plus they generally come in muscle-supporting, quick-drying, breathable fabrics. Neopro makes a decently affordable, decent quality, gender-neutral option. I really love my team’s Jakroo bibs, and Velocio offers a variety of excellent upgrade options with easy bathroom access. Don’t wear underwear with padded shorts. If you’re wearing underwear and any other type of shorts, be mindful of seam placement for chafing reasons. Consider a chamois creme to help lubricate and protect skin on longer rides.
I like merino when I’m riding as it dries and regulates temp better than cotton but doesn’t get as stinky as synthetics. It’s pricey but can be pretty durable, so consider investing if you don’t mind wearing the same pieces more often.
I LOVE my Patagonia Houdini jacket. Catch it on clearance (or eBay) if you can, it packs so tiny and has saved my skin several times. When looking for a windbreaker, look for one that has a nice tall collar and long enough sleeves. If you’re using a rain jacket as a windbreaker, be aware that it will not breathe well and you may get just as wet from sweat as you would have from rain. Consider skipping in warm weather and in cool weather, look for a jacket that has zippered vents or even a poncho-style rain cover.
I recently learned my affordable jacket isn’t made any longer, alas! Look for a high collar, durable water repellent, reflective bits, and long sleeves/tail. Most bike-specific jackets won’t offer hand pockets, so beware! Consider looking for a 2-way zipper and/or pit zips for temperature management.
I wear mostly Handup gloves. They’re unpadded but work with touch screens and provide grip for brake levers. I have worn full-finger and fingerless versions of padded Giro and Pearl Izumi gloves in the past but currently want grip without padding. I always end up wearing men’s or unisex gloves because I have long fingers, so don’t get hung up on gendered labels for clothes.
I wear the Handup ColdER weather gloves for a good variety of conditions. Previously and for several years I wore Pearl Izumi cyclone gel gloves. They’re more padded, a little more dexterous, but less insulated and frankly less cute.
I wear the 45NRTH Sturmfist 4 Cycling Gloves. These are admittedly a bit of an investment, but I have seen them on sale for under $60 a few times. They’re very warm, offer great wrist coverage, dexterity, and are smartphone compatible. Previously I used Pearl Izumi lobster gloves which are also nice! A little less durable, water resistant, and with a lining I like a bit less.
Make sure they’re stretchy enough for you to lift your leg and bend your knees and waist! High-rise pants are nice so you’re not exposing your low back/butt. Stay away from cotton/ denim if possible and consider wind blocking and breathability relative to conditions.
I have a pair of Pearl Izumi softshell pants that have lasted years and are cozy to shockingly low temps. They’re windproof on the whole front, stretchy on the back, and have a nice, fleecy brushed interior. Certainly a worthwhile investment for regular cold-weather riding.
A lot of people like wearing buffs or generic neck rolls. I have a merino one from Pearl Izumi that I mostly wear off the bike or when it’s extremely cold. In all but the most extreme cold temperatures, a buff makes the back of my neck too hot, so I prefer a bandana tied into a triangle around my neck. The front offers customizable wind protection that I can position based on temps, from covering my nose/mouth when it’s really cold to pulled down and out of the way if it’s warm.
The goal is to keep and/or move moisture away from your skin. Different materials will be better or worse at this. Cotton is particularly bad, it absorbs lots of moisture and holds it, meaning you’ll just stay wet. This is potentially disastrous in cold conditions—see more below. Some natural fibers like silk and merino are better at wicking moisture, moving it from your skin to the outside of the garment where it can evaporate most easily. Synthetic fabrics (like polyester) can also do a good job here. Synthetics (polyester, nylon, spandex, etc.) and semi-synthetics (rayon, modal, lyocell, etc.) are extremely varied and their properties depend on the specifics of weave and production.
For longer rides and/or rides where you will stop for some time in the middle, you’ll want to be extra careful about moisture management and layering. Thinking about the temperature at your stop location, how long you’ll be there, and whether there will be any opportunity to dry or warm your clothes will impact the clothing you should wear and/or bring. If you’re stopping for coffee and will be in a warm café for an hour, consider taking off as many layers as possible and spreading them out/hanging them to dry. If you’re in a lukewarm grocery store, take off enough so that you’re not sweating inside, but don’t let your body get cold as your heart rate drops. If you will be standing outside in the cold, consider bringing something like a puffy jacket and dry gloves or hand warmers, since staying warm when still is a completely different game to staying warm when exercising and moving through wind.
When you reach a destination where you’ll be staying for more than an hour or two, I strongly recommend changing clothes ASAP! This is prudent as staying in sweaty clothes is gross in any season, but in the winter, it’s easy to get chilled even in a warm environment when you stop exercising but stay sweaty. If you wait too long and get cold anyway, hopping in the shower can help reset your temperature quickly. You can also do some jumping jacks or whatever, but simply putting on dry clothes can be magical.
While cotton is a lovely, natural material, it is not well suited for outdoor activities. It absorbs sweat and holds it and loses even its meager insulating properties when wet. If it’s next to your skin, it’s going to hold your sweat next to your skin, chilling you indefinitely. If it’s on a contact point (seat, feet), it will also increase friction and create a home for bacteria. It will be heavy, wet, and cold. Other materials like merino wool, silk, and synthetic materials designed for athletics will pull moisture away from your skin, transport it to the surface of the material to evaporate, and can maintain insulating properties, even when wet. UNFORTUNATELY DENIM IS MADE FROM COTTON, as are many underwear brands. I know it looks cool and natural fibers are good. you can make your own judgements on fashion vs. function, but you should know the rules before breaking them.
My partner who used to work in kitchens taught me about “chef hands”, where people working in kitchens can handle items much hotter than the average person can. Partly this is about calluses, but it’s also about practice and understanding the difference between discomfort and damage. Hot and cold conditions are uncomfortable a ways before they are an immediate threat to health or safety. I’ve had numb fingers and toes and face many times but thankfully have never had hypothermia or frostbite. Generally, if it’s cold out and you are comfortable at the beginning of your ride, you’ve dressed too warmly. It can help to brace yourself for a little discomfort, and then learn to ride through it, but understanding when you’re in danger is crucial too. Nobody thinks you’re extra cool for getting hypothermia!
Pre-heat your clothes, especially shoes & gloves! If you have radiators or somewhere particularly warm, I strongly recommend storing your shoes & gloves there before leaving for cold rides. And every time you’re getting ready to get back on the bike, make sure to stick your gloves in your armpits, inside your jacket, or between your legs to warm up before putting them back on (these are also convenient spots to hold your gloves while, for example, you’re unlocking your bike). This is most crucial if your gloves are already a bit sweaty. Cold damp gloves don’t work well, but pre-warmed damp gloves, honestly fine.
Bike-specific gear can help as it will be designed for riding position. Not always crucial, but when layering heavily it becomes more important/helpful. Arm position, waist/hip mobility, and knee flexion are the spots that get most challenging. When trying a new layering combo, make sure you can bend where you need to before you fall over trying to swing your leg over the bike. Additional layers will also make every pedal stroke a tiny bit more difficult, so be mindful you’ll need to balance conflicting priorities.
For longer rides in the cold or if it’s cold and raining, you can wear latex or nitrile gloves under your insulating gloves. This will generally keep your hands from getting cold and will keep your gloves from getting wet with sweat, but if you need to use your bare hands at any point, the gloves will be impossible to put back on. Plus your hands will get pruny from sweat. Functional, but not long-term comfy. Similarly, plastic bags (even wrappers from granola bars or chip bags) can be worn over the socks but inside your shoes in an emergency. A plastic bag under your jersey in the front can form an emergency wind shield. These things aren’t necessarily comfy but it might be worth the awkwardness if you’re caught in the cold.
If you’re on a budget, consider shopping for winter clothes in spring when they are most likely to go on sale. If shopping used, keep in mind that technical waterproof fabrics can lose waterproofness over time, but can often be refreshed with products like Nikwax Tech Wash and TX.Direct.
I recommend taking notes on your experiences with various clothing. Taking my own notes while preparing this guide ended up being a huge help for me, and I appreciated having my notes in front of me when getting ready in the morning. Toward that end, I've prepared a template you can use if you want to print something out. You can also keep notes in a notebook or as I did, in a spreadsheet. Find the printable template here.