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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