Head to Toe Guide to Winter Biking Gear

The key to a comfortable winter ride is to stay warm and dry, which means having the right quality gear.

So, what should you wear?

Well, the answer isn’t as straightforward as you might think. Gear is a highly subjective matter, and fortunately there are many options these days for helping you stay warm and dry, all winter long.

Let’s break it down from head to toe.

First Off – Wool

You’ll see us recommend a lot of wool below. While tech fabrics can do their job in some situations, the rainy weather of Portland presents additional challenges that are best handled by wool, a natural fabric won’t stink up nearly as easily. Many people find that it’s just also much more comfortable. What about the scratch? Forget that wool of your childhood: these days most wool, especially wool used in riding gear, is soft and cozy.

Head and Neck

Head band – keeps your earns warm snugly, your head a little warmer, light under a helmet, easy to carry.

Light weight wool beanie – we particularly like the Chase Beanie from Icebreaker. Not bulky under your helmet, covers your ears lightly.

Balaclava – just a little of your face is exposed, cozying-up your head and neck all in one. A cycling-specific one will be light weight enough to fit well under your helmet.

Head/neck band – A loose neck band, Smartwool makes one, that doubles as a head band is a nice feature. Get one that’s very light weight wool and can expand to cover your entire head if need be.

Helmet cover – They surely look a little silly, but a helmet cover will keep your head warm and dry. However, most helmets don’t allow in a ton of rain. Whether the effectiveness outweighs the aesthetics if for you to determine.

Hood – A light weight hooded wool sweatshirt is an excellent way to go. Pull on that hood, strap on your helmet and you get the added bonus of cozy neck coverage and a tucked-in warmth. Add an additionally waterproof layer to your torso (see below).

Scarf – A simple scarf can work well. We recommend a light weight wool scarf that is not too bulky. Wrap it around your neck once and tuck the ends against your chest before zipping up your jacket for a cozier feel. In a pinch, this can double as a head cover for additional warmth.

Don’t forget to adjust your helmet to allow for a safe and comfortable fit over whatever warms your noggin.


Stack your torso in layers. Start with an extremely lightweight wool underlayer against your skin (on cold days), then your regular clothes with a shirt and something warmer on top. Top it off with your waterproof outerlayer of choice. If you get warm during the ride, you can remove layers as you go.

Tech Jacket – Fully water proof and breathable is key here. You’ll probably spend $100-$275 and the jacket should last yo at least four years of regular commuting in the rain, so long as you follow the manufacturer’s washing instructions. If your jacket fails before then, you should file a complaint.

Waterproofing is the easy part, adding in the breathability is where things get expensive. As you go up in breathability, your fully waterproof fabrics go up in cost. So when you see a very expensive jacket, in a lot of cases it’s not a scam, it’s really comfortable. If you like to ride fast and work up a sweat but still want to ride to work (or simply clock some serious miles this winter), the investment is well worth the cost.

Thick wool jacket – A nice wool jacket (think pea coat style) is an excellent choice for staying dapper and dry on your ride. So long as you’re not a speed racer, this cozy option allows you to dress down underneath and look good on top. After a while in heavy rain the water will eventually soak through, but you’ve got a good hour in light drizzle.

Thick wool sweater – Oh those cast-off shrunken sweaters at the Goodwill! What a find! A sweater that has been accidentally shrunken has a denser materials, which means it will do a better job of keeping the rain at bay. This works particularly well on light drizzle days.

Rain cape – Rain capes look a little silly, but they’re are extremely comfortable and effective. They cape extends to your hands, providing coverage over your legs. You may not need to worry about leg coverage with this option. Capes also have the maximum airflow, meaning you won’t get sticky, sweaty and stinky underneath.

Wool hoodie – A wool hoodie, like the awesome, thin Merino Pasha by Chrome or the various weighted styles Icebreaker carries, are an excellent choice for light misting days or short rides. The option of a hood for cold days is excellent. They won’t keep the rain at bay for long, but they’ll do the job for a few miles in light rain.

Can your hooded hiking/Oregon jacket double as your bike jacket? Maybe, but in most cases hiking style rain coats aren’t breathable enough for riding, or they’re too stiff to be comfortable for fast, performance-style riders.

Will your rain jacket have a hood? Probably not. Surprisingly few of them do. Showers Pass’s aptly named Crossover and Endura’s Urban Shell (love this jacket) and MT500 do have hoods.


Thin shell – Pearl Izumi and other brands make a great waterproof shell that’s much like a rain jacket for your hands and can slip over any other gloves. We like these for their versatility; you can increase the warmth of your under glove as the weather gets colder. We like a wool liner underneath or cheap stretchy kids-style gloves on warmer days.

100% waterproof – Warm gloves are useless in Oregon unless they’re 100% waterproof. That combo is not easy to find. We could do (and have, years ago) a whole article on gloves alone. We plan to revisit the topic soon.

Neoprene – Neoprene is used a lot in bike gear. The fabric locks in warmth, but your hands won’t breathe at all. This means your hands will be a little damp, and might wind up getting cold from that, or will simply feel a little gross and clammy. Still, this inexpensive, flexible option is a preferred by some riders.

Cheap stretchies – On days that aren’t really rainy or cold, we love a pair of cheap stretchy gloves, the kind that are sold at kiosks in just about every convenience store or Walgreens all winter long. These gloves pack small and at $5 it’s easy to have an extra pair here and there (office, your extra bag, etc). They will last you a couple seasons before you blow a hole in the index finger; without fail, that’s where the fabric always wears out). Use that opening for greater ease when navigating your touch screen device and you might find that you sort of like the worn-out glove.

We can’t say much more than that. Within the glove category there is a vast array of options. We promise, that glove article is coming soon!


If you’re using a rain cape, you’re good to go. Just don some warm pants and socks, or fleece-lined tights for the ladies.

Rain pants – These are standard issue, but many people find them cumbersome and a hassle.

Wool riding tights and waterproof pants – Some people prefer wool riding tights and a tech knicker, like the Telegraph Knicker from Chrome, but usually this means changing your pants when you get to your destination, unless you’re a total bike geek who hangs out in this stuff all day long (you know who you are). Fortunately it’s a pretty good casual look, so no style points are lost.

Wool base layer – No matter what you wear on top, a pair of thin, wool tights (for men and women) are essential on extremely cold days if your legs get chilly quickly. Icebreaker makes very think ones that fit comfortably under even fitted pants.

Thick wool pants – They’re not for everyone, but if you can find a pair of wool pants that fit your style, they’ll work well on misty or drizzly days when you don’t have far to go.

Quick dry tech – A tech fabric that dries quickly works well if you’re not going to get drenched out there. Add a wool underlayer for warmth and you’ll dry off rather quickly at your destination.


Many people find it extremely challenging to keep their feet dry, but it doesn’t have to be.

Wool socks – start here for maximum warmth.

Rain booties – various styles exist, and are a great way to keep your feel completely dry on your ride.

Galoshes – Seriously. These old-school flexible boots will easily fit over your shoes. Cinch them down at the top with a velcro leg strap or tuck them inside your pant legs. You might find they’re more comfortable than rain booties.

Boots – Straight up rain boots can be a little uncomfortable to bike in, but you might be able to find alternate styles that are a little more flexible, like the wet weather boots offered by LL Bean. You might need to change shoes when you get to your destination, but nothing beats dry feet, especially if you have to sit in an office all day or you’re at a dressed-up function.

Extra socks – Keep extra socks in your desk at work. In a pinch, you can probably slip off your soggy shoes and wear socks at least while you’re sitting at the desk (or while walking around, if you have that type of office). Get a little of the damp out of your shoes using a hand dryer or hair dryer, but don’t expect your shoes to be dry by the end of the day, making for an unpleasant ride home. These types of discomforts are what make people reluctant to ride – so avoid them at all possible costs.

Toe warmers – Going on a long ride? Consider toe warmer packs. Buy them in bulk and you’ll wind up putting just a few dollars into securing the warmth of your tosies as you rock that hundo. Totally worth it.

What do you wear?

How do you stay warm and dry on your bike, all winter long? Share your ideas below.

How do you stay warm and dry on your bike all winter long? We’re running an extensive series of articles with everyday cycling tips to help you #KeepRiding no matter what the elements throw our way. You can read the entire series here and follow us on Twitter and Instagram for even more cool ideas. Hash tag your posts #KeepRiding and inspire more people to ride their bikes this winter.

12 thoughts on “Head to Toe Guide to Winter Biking Gear”

  1. Wow, that is a freakishly long list. I don’t know how far other people ride, but the helmet covers are horrible things for me (actually, almost anything waterproof). 8 miles one way, so my head gets extra sweaty under the helmet cover. I much prefer to be wet from rain than sweat. When I do want to keep the rain off, I use a good old poncho, which keeps me dry, allows air flow, and keeps me cool. I’m not going anywhere fast (I’m commuting, not racing, thanks). Other than that, just about anything goes, nothing special needed, I just change when I get to work. I did get some lobster gloves for the coldest days, but haven’t tested them, yet.

  2. A helmet cover is good, but you’re going to put it on and take it off as the weather constantly changes around here. I use el cheapo clear shower caps, with small holes to aid circulation. Use a pen to poke holes front and aft, take t off when not needed and stuff in the smallest of seat bags. You can even use it to cover your saddle.
    Another innovation is a return to the Ascot. Instead of a bulky scarf that can start flying in the wind, add a stylish Ascot tucked under your shirt and jacket. They are almost all made of silk, and feel great. They look good too. Select a color that creates a contrast with your jacket for that unique look.

  3. Joe – it’s a necessarily long list. There are many options. I tried some of these in the past and found I didn’t like them (helmet covers! Everyone told me I HAD to have one and it was awful. but some people like them – it is subjective, like said above). I like that there are options presented so I can make my own decision. I never thought about wool so much as in the last couple years, seems like people talk about it now more than they used to in the 90s when I started biking

  4. Best Winter apparel item ever: my Gore-tex oversocks! They fit right in my shoes over a lighter sock, keep my feet dry no matter what the state of my shoes. Love ’em!

  5. George Letchworth

    When staying at hotels collect the shower caps and keep them on your bike. The shower caps fit over your helmet keeping your head warm and dry on the occasionallly rainy day in Oregon. They can also be used as seat covers. In a pinch you can rubber band them over your shoes. Never tried them over the gloves but there will be a first time.

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