How To Be A Winter Cyclist While Staying Warm And Safe

I ride my bicycle more days than not, including during Chicago's endless icy winters.

I never managed to acclimate myself to any athletic endeavor before I discovered biking. Running half a block left my lungs blood-raw and smoldering. Any round object thrown at me was much more likely to be met with flinchy cowering than anything attempting a catch. But I ride my bicycle more days than not, including during Chicago's endless icy winters.

I'd love to be an athletic machine: seven feet of sinew dunking on the entire WBNA, an elite runner, some dude with overzealous calves riding up a mountain on European television. Instead, I'm showing up to the bar in the middle of winter in Matruska doll layers of black merino wool. I think that's enough for me.


Unless you're getting ready for The World Naked Bike Ride (NSFW), the first step in preparing to ride your bike is getting dressed. Cyclists have different needs from your average winter warrior. We need our clothing to stretch and move with us to allow for greater mobility. We need it to breathe, so we're not drenched in sweat; we need it to block wind, so that sweat doesn't turn ice cold as soon as air hits it.


I recommend wearing a well-ventilated helmet that uses a dial to adjust fit, like the Giro Atmos or Aeon. This way, you can keep your head cool during the summer, and fit a hat underneath during the winter. Your hat should cover your ears.

If you live in a place that's cold enough for your face to feel like it's going to fall off when you walk outside, you're going to want to keep it covered up. Stretchy tubes worn around your neck that can be pulled up over your face go by various monikers such as neck gaiters, winter collars, cowls, and buffs depending on the retailer. The nuclear option is Trash Bags' custom face masks. They were developed by a Minneapolis bike messenger, so you know they've been road tested in abhorrent conditions.


The most important factors for covering your torso are your base layer and your outer layer; you can wear your everyday clothing between them. Biking in winter doesn't necessarily mean looking like you're exploring the Andes.

I have absolutely noticed a difference wearing long-sleeved shirts made of merino wool or proprietary tech fabrics (such as Columbia's Omniheat) as the layer closest to my skin. Yes, they're expensive, and not the most stylish threads in the game -- but if you're mashing around in temperatures below freezing, the superior wicking and warmth really help. The last thing you want to do is wear all cotton and let it get soaked with cold sweat.

During fall and spring, I can often get away with wearing just a t-shirt over a base layer, or a shirt with a wool or cashmere sweater over it. Yeah, I said cashmere. Don't start a proletariat uprising just yet; you can usually find mad deals on fancy sweaters at liquidators like Filene's, TJ Maxx, or Marshall's after Mother's Day or Christmas as department stores try to get rid of all the mom gifts that didn't sell.

Once the weather turns really cold and precipitation comes into play, you need an outer layer. You do not need a cycling specific jacket or a particular brand. What matters are these criteria:

  • Sleeves long enough to cover your wrists when your arms are outstretched
  • A torso long enough to cover your lower back/upper butt when you're bent forward
  • Wind resistant
  • Water repellent
  • Underarm zips (Optional -- to give your pits some breathing room when you're on a hard ride but still need protection from the elements)

(You can read about this stuff in more depth here).

Whether you want your everyday jacket to be waterproof depends on preference and how rainy the area you live in is. The drawback to truly waterproof clothing is that is generally less breathable than other materials, and that waterproofing wears off (usually in areas that bend a lot or take a lot of friction; with cyclists, this is usually the arms and the shoulder where your messenger bag rests).

You can refresh the waterproofing on your garments with wash-in products such as NikWax, but I highly recommend buying any waterproof coat from a store with a lenient return policy like REI or Patagonia. It's better to buy an item at full price if you can manage it and get a replacement every time it wears out; save the online outlet discount shopping for wool socks.

I personally have a thin shell that isn't very warm -- but it blocks wind and rain. I layer it with a puffy packable jacket that is extremely warm and slightly water repellent but not suitable for heavy rain. This way, I'm equally prepared for summer thunderstorms and winter blizzards.


There are many options to keeping your legs warm, depending on your needs and personal style. Smartwool tights are amazing, either on their own under a skirt or layered under jeans. Long underwear and flannel-lined jeans are both game changers.

And if you are a serious winter cyclist, I can't recommend investing in top-of-the-line thermal bike tights highly enough. Pearl Izumi makes some that are waterproof, windproof, and fleece-lined. They're over $100, but these indestructible suckers have endured years of me wearing them literally every day I bike through the worst of winter.

Hands and Feet

Lastly, we've got the extremities. I recommend purchasing two pairs of gloves: a light stretchy pair of fall/spring gloves, and a super heavy pair of waterproof winter gloves. Carry them both at all times -- that way if you lose a pair or one gets wet, you have a back up. In extreme weather, you can wear your thin gloves under your winter gloves. This also allows you to pull off your winter gloves to unlock your bike or find your keys without exposing your bare skin to the cold.

If you're someone who's always walking around with ice cold crypt keeper hands (you know who you are), I recommend getting gloves that bundle fingers together. Your hands stay warmer when digits can share warmth. Besides mittens, there are also lobster gloves, which are mittens with a freaky-looking split down the middle. Sometimes you can find cycling-specific "trigger finger" gloves, which bundle your pinkie and ring finger together but leave your middle and index finger free to work your brakes.

If you use clipless cycling shoes, you probably know what you're doing enough that you don't need my advice. If you wear regular shoes while biking, buy them large enough that you can still wriggle your toes while wearing thick wool socks. Thick soles with heavy tread are a necessity if you live somewhere where it snows.


That wobbly riding you see people on too-small bikes doing, weaving everywhere with their elbows and knees akimbo? Or that swoopy, Premium Rush, fixed-gear-for-life look-how-cool-I-am style? Don’t do that. Don’t lean, or weave, or wobble. Keeping your back, arms, and legs in alignment will keep your weight centered over your bicycle and make you much less likely to wipe out.

Vertical Thoughts

Ice and snow can be intimidating to ride on, I'm not going to lie. All your instincts tell you that you're going to fall. There are indeed conditions that I won't ride in; I wrote extensively about how to tell if it's safe to ride here. But during most of the year, all you need to overcome your fear is to think vertical thoughts.

What does thinking vertical thoughts mean? If you're going over something that makes you more likely to faceplant -- a wet grated bridge or manhole, a frozen chunk of dirty snow, a puddle -- imagine there's a pool cue strapped to your spine, keeping your back straight. Or imagine an invisible string, attached to the top of your head, that pulls you perfectly upright from the sky, like a puppet. Visualize yourself PAST the obstacle. Don't concentrate on the ice you're on; concentrate on the pavement just past it.


All the lessons about thinking vertical thoughts you just read? They apply a thousand times over when you're turning, especially if it’s slick and icy out.

When you're taking a corner, steer with your handlebars, not your body weight. Stay as upright as possible to keep your body weight centered.

Slowing Down

If you need to slow down to take an icy corner, do it before you get there. Brake early enough that you're at a safe speed before you even hit the stop sign. Don't ever hit your brakes while you're taking a corner, and don't lean into the turn; keep your posture perfect, and think vertical thoughts.

Being Willing

Everything I've described comes second to your willingness to brave the elements and have fun on your bicycle. You can have a wardrobe fit for a Himalayan expedition, but if you secretly dread riding your bike, no fleece-lined rain pants are going to change your mind. And if you're determined to extend your torrid summer fling with your bike long into cuffing season, you'll find a way to do it even if you have to carefully plan your route along plowed streets.

I firmly believe that if I could teach myself to ride a bicycle as an adult in an urban environment in all seasons, anyone can. I'm no lycra-clad crusader, just a femme who loves their fixed gear.

If you'd like to read more about biking in winter, my feminist bike gang Tiny Fix has got you covered. Every one of us rides our bikes during the winter, and if we can, so can you.