Cold-Weather City Biking: Suggestions & Some New Finds

The snow and cold have come full-on to Chicago this December, which means every bike blogger has been getting out his or her winter bike/gear/accessories and then writing about it.  I’m no different however this year I have had to do some reconfiguring  since I’ll be riding on Oma – the Dutch bike I bought this past fall.  In previous winters I tooled around the city on my trusty Trek mountain bike. I already had a lot of winter gear, but because I can wear more ‘normal’ clothes on Oma,  I’ve actually had to come up with a couple of new wardrobe configurations.  Here’s what will be getting me through my city riding this winter:

  • Layers: Everyone tells you this, and it’s worth repeating.A couple of layers (t-shirts, fleece, wind/rainproof coat) serve you much better than one big winter coat.  In previous years on my mountain bike I wore an unlined, very over-sized, nylon windbreaker with an elastic bottom and elastic cuffs over a couple of shirts. I added a fleece when it was really cold outside , like below 20 degrees Fahrenheit. On Oma, I’m usually wearing the lovely black cloth coat that I wore in my Bike Fancy photo op, over a sweater and a shirt or dress.  So far I’ve tested this combo down to about 12-15 degrees Fahrenheit and it’s kept my core plenty warm.
  • Head: Gotta keep your head , ears and face warm. This was not new to me, but I added a new helmet this year – a Bern helmet.  I bought the white Men’s Brentwood helmet. Instead of wearing a stocking cap underneath  I purchased the winter insert that goes with it. Next year I may get the plain hunter style instead, or one of the cool fleece hats from Fabric Horse.


  • Face: In past years a stocking cap on the coldest days along with a neck warmer kept my body heat in and wind away. This winter it hasn’t quite been enough – not sure if that’s because I’m sitting upright and taking the full-force of the wind on my face or what, but my face has gotten quite cold when the temperatures have dipped down into the 20s.  All the balaclavas I’ve tried in the past felt too bulky and goofy so I choose not to wear one.  Recently though I was at Rosoce Village Bikes and they had a couple of these thin, lightweight balaclavas from Craft. I tried one on and even though I look ridiculous it does the trick.  PS:  a lot more of your face can be visible than appears in the picture on the Craft site.
  • Neck: Because I’m now wearing a winter coat the doesn’t come all the way up to my neck like the windbreaker did, I am now  wearing a scarf instead of my fleece neck warmer.  I don’t like the idea of wearing a scarf on a bike – something about Isadora Duncan’s tragic death comes to mind – but a scarf alone or with a balaclava seems to work better at keeping my body heat in and the cold out, than just a neck warmer.
  • Hands:  This was a big challenge for me last year and I’ve been asking other cyclists how they keep their hands warm since my old standby Lake brand winter bike gloves couldn’t keep my fingers warm last winter. Everyone unanimously said something that was wind and waterproof, and that the specific brand or type didn’t matter.  Just find a style that fit your hands and was comfortable on your bike. Turns out that I actually bought winter gloves last spring at a bike gear sale somewhere. I found them when I was going through my winter bike gear. It was a nice surprise.  These Typhoon gloves from Garneau are working well for me this winter when layered over some regular knitted gloves.


I have large hands, so I bought the XL gloves and they fit nicely over some cute knitted gloves that I have.  And I can still lock and unlock my bike with the gloves on.  I call them my lobster claw gloves – sci-fi fans might say that there is something decidedly Vulcan about them too.

  • Legs: I like to wear dresses and skirts a lot, and the fact that leggings are back in style has been one fashion from the 80s that I am happy to see return. For cold-weather riding I’m now wearing tights under leggings or leggings or tights under jeans. Lucky for me I discovered a couple of new sources for cool tights for tall and/or plus-size fabulous women like myself.  First there is the site We Love Colors which carries footless tights in all sorts of colors as well as sizes.  I ordered a pair of these blue swirly tights that should look nice with black legwarmers or leggings over them ( the picture comes from the We Love Colors site by the way).


Second,  I came across Sock Dreams which has a fairly wide selection of stylish thigh-high socks and legwarmers that will look good over tights, leggings, or jeans. They have socks and leggings for women, men (!), small feet, large feet (some up to size 14) , tall and plus sizes. I’m getting some super tall thigh-high striped socks that should keep me warm this winter (photo courtesy of the Sock Dreams site).


PS: I discovered these sites via two fashion/cyclist bloggers that I recently discovered. Thanks to Fiona at A New Me and Vanessa at Big Girl. Small Budget. Tiny Town.

  • Feet: As much as I would love to get some Sorel Cate the Great boots, my 5-year old, plain brown Uggs are still in fantastic shape and keep my toes incredibly warm. I have a pair of the Women’s version of this Men’s Beacon Boot – mine are a little more refined and the sole is not quite as chunky.


Not super pretty, but definitely super-warm.  If it’s not too cold out though, I’ll wear something a little more stylish like riding-style boots, cowboy boots or my Frye harness boots. So, to sum it up,  Layers + keep your extremities warm and you’ll be good to go this winter. How do you manage to keep warm on your winter commutes?

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  • ladybug

    I’m with Ash on cotton, but I have to go a ways on my commute and I heat up. I use thin wool layers over each other- like a thin long sleeved t-shirt weight shirt under a thin lambswool weight layer under my waterproof jacket. Thrift shops are a great place to find a mix of wool layers in sizes to fit all bodies in many different weights so that you can match the layers to any kind of day. Good finds lurk in the men’s sections. I wear wool dresses often over tights if the weather is right, with a thin layer of polypropylene or wool underneath. Sales are great in the very late winter or early spring clearance on any winter riding under layers bought new. The trademark has expired on GoreTex so cheaper jackets are out there now that do the job of jackets that were once very expensive for your waterproof top layer. Careful washing is key to keeping expensive layers useful in the long run. I don’t put my under layers of wool or poly in the dryer and they last a long time. Wool socks if you can’t find fleece!

    • Samantha

      Ah yes, any excuse to go thrifting is a good one!

  • SM

    Yes, you and the other ladies definitely inspire me to ride in the cold weather. I like those long socks that go over the tights.

    • Samantha

      You should give it a try though it sounds like your route to work isn’t too safe when there is snow/slush/ice. And yeah, I’m excited about those long socks too.. we’ll see how those work out.

  • Madeline

    One item you didn’t mention is eye protection. My eyes were feeling like they were going to freeze solid and pop right out of my head. Plus the wind made my eyes water so much I could barely see. I wear glasses (and I’m really nearsighted), so swim goggles or whatever weren’t an option. Prescription goggles I looked at online were pretty expensive and I wasn’t sure I wanted to go that route. Then someone suggested safety goggles like people use with power tools. I went to Home Depot a few days ago and picked up some cheap (like $3 cheap) clear plastic goggles, and they’re the bomb! No more tears! No more frozen eyeballs! They’re ventilated just enough and they fit over my glasses just fine. I can ride down the road in sub-freezing weather and between the balaclava and the goggles my face feels like it’s sitting in its own warm little living room.

    • Samantha

      You are right – I didn’t mention goggles. I should have asked about it. I wear glasses and I’ve never worn goggles – never thought about wearing goggles at all…just put up with the eye watering that happens at times. I really like your Home Depot trick – sounds perfect. My question is though, do they fog up, can you see well out of them on all sides, etc? That’s what i wonder about.

      • Madeline

        So far they haven’t fogged up on me as long as I wear them in a way that doesn’t funnel my breath directly into them (i.e. I have to watch how their edges meet up with the opening in my balaclava). They have little vents that can probably be enlarged if fogging becomes a problem in colder weather. The visibility is very good. They’re 100% clear plastic including the sides. There’s a visible outline where the sides meet the front but it’s similar to being able to see the frames of your glasses when you wear them. I’d upload a photo of them if I knew how to do that on here. FWIW, the eye-watering thing may be somewhat age-related; I’m a bit older than the typical cyclist and my eyes are a lot more sensitive to wind and cold than they used to be.

      • Samantha

        Good to know – thanks for the info Madeline! I rode this am in a slight snowstorm and I did OK with just my glasses. I think I’ll keep your Home Depot trick in mind though.

  • Timoohz

    Grr, I lost my good reply because of captcha failure 🙁 So you’re going to get my bad reply.

    Army boots, thin socks. Long sleeved underwear, jeans, shirt, jacket, wool hat, ‘autumn’ gloves. Good to 15F, -10C.

    Thicker socks. A balaclava, winter mittens instead of autumn gloves.

    Add Sweatpants under jeans or windproof trousers over jeans. A hoodie. Long sleeved leather mittens. Jacket hood up.

    More socks. Add sweatpants or windproof trousers, which ever you did not put on earlier. A fleece shirt under the jacket. Scarf to protect the face.

    Colder than that: the rubber in the tires is not elastic anymore and the energy losses to deformations is so big that I need to keep pedaling to keep the bike moving even in a steep downhill, like in all those underpasses. All that hard work means I start to sweat. While moving that is not a big problem. If I have to stop at a traffic sign, my glasses will fog up because of the scarf. The fog will freeze when I start cycling again. Repeat a few times and I can’t see anything. So I usually walk if it’s colder than -30C, -22F.

    • Samantha

      Sorry about the captcha failure.. I’m thinking about switching to Disqus for comments instead.

      Sounds like you have your winter riding wardrobe down! And you ride to -22F? WOW! I stop riding at about -5F. How often is it that cold up north there Oulu? I mean I know you’re very far north, but still -22? You probably keep walking and don’t stand and wait for a bus in those temperatures!

      • Timoohz

        Again: “ERROR: Could not read CAPTCHA token file.”

        Anyway, the high pressure/ low pressure areas move and they change the direction of the wind. Wind from west or south= warm weather, maybe even above freezing. Wind from north brings cold air from the north pole and wind from east brings cold air from the Siberia. Then we can get -40C, -40F. In general, we get a few weeks of temperatures below -30C, -22F every year. The monthly average is a little below -10C, +14F which is not bad at all.

        That -4F, -20C is the limit for most winter cyclists here in Oulu too, so don’t feel bad. I can do a little colder because my trips are so short. For me, the energy-sucking-tires effect is a more important limiting factor to cycling than cold weather. I can dress up, but I don’t have wool hat for my bike :-/

  • Vanessa

    I don’t know how you do it, riding in winter! You’re an inspiration to me, your much weaker friend on the other side of Lake Michigan.
    Thanks for including my link… if I get brave and try a winter spin, I’ll let you know!

    • Samantha

      Thanks! You get a lot more snow over there than we do, so do let me know if you venture out. Stay warm and stylish!

  • Cecily

    I can’t find any wool items that fit me in Vancouver, the Town of Tiny Tushies. I can barely even find wool socks and gloves to fit my huge hands and feet.

    I used to complain about the sheer amount of polyester plus size clothing available here until I started riding my bike and realized just how quickly polyester dries out. Unlike wool, it holds on to odors more readily, so you may have to buy new polyester/nylon base layers more often, but I’ve discovered that those poly-blend camisoles that are so easy to find in plus-size shops make the perfect base layer.

    • Samantha

      Hmmmm.. I never thought about a camisole for a base layer… might be better than a long-sleeved whatever. I may have to give that a try, especially since they’re easy to find.

  • Ash L.

    I second most of what you’ve written except for wearing t-shirts and fleece as a base layer. Fleece and cotton both get extremely wet with sweat and will make you very cold if you plan to ride more than a couple of miles when you’ll perspirate. When it’s below 25 I always wear a Capilene (any poly will do but this one i nice and thin) or wool/cashmere base layer. These materials are naturally wicking and neither will hold much odor so you can wear them 3 or 4 times before you have to begin thinking of washing them. Wool is especially warm too, like a bug in a rug, so if I wear a wool base all I need over it is a thin shell wind breaker.

    This is the first year that I’ve started making fleece socks (from my left over BikeWinter fleece reserves) and I have to say that they are fantastic over a pair of thin athletic socks for that extra warmth without the bulk.

    • Samantha

      Good point! When I was wearing t-shirts and fleece in previous winters I didn’ t worry about sweat because I was always changing clothes/cleaning up once I arrived at my destination (usually the office). Now that I’m riding a city bike instead of a mountain bike, I’m riding more slowly and I don’t put in tons of miles so my base layers can be cotton if need be, since I’m wearing ‘regular’ clothes. Capilene or wool base layers though are best, as you mentioned. And your fleece socks sound very warm and cozy. Perhaps we should start making Bike Winter socks and balaclavas?

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