Winter Bike Fashion: A Recap

This year marked the first time I biked through a winter in Madison. It was great for my calves, but showing up to any event looking presentable was definitely more challenging!

I’m not the only one turning to the closet and struggling to find clothes that work for work, play and inclement weather. According to the 2008-2012 American Community Survey, Madison is second among large cities for people who bike to work. We have great bike paths in the city and beyond, but there’s no public agency dedicated to helping us traverse our closets.

Posts on bike friendly fashion abound, but few address winter biking. For the most part, I was on my own. The secret, I learned, is one easy word:

LAYERS. They solve everything.

For those contemplating (or already decided on!) winter biking next season, let’s break it down:

Base layer: Long johns. This might be the most quintessentially midwestern recommendation on a blog that’s supposed to be about moving beyond midwestern stereotypes, but a good set of long johns keeps everything happy. I wore Cuddldud bottoms every day when I biked this winter, and if it was below 10 degrees, I added a Cuddlduds top layer, too. The material is thin, remains unnoticeable under my clothes, and is designed well enough to stay relatively cool during the day while keeping me warm during the commute.

Cuddledud Bottoms

Second layer: Regular clothes. This layer is pretty easy if you’re already comfortable dressing for biking. For me, that means starting with a good pair of straight legged or skinny jeans. My favorites are a pair of True Religion jeans that have loosened up enough to move well but are sturdy enough to take the rub of my bike seat.

Any sturdy pants also work well, and for formal meetings, I’ve worn dresses with pants underneath, quickly stripping the pants and tucking them into my bag when I get there.

True Religion Jeans

On top, my favorite thing to wear is a thin wool sweater or lightweight blazer (depending on the event) for warmth without bulk.

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I also typically wear SmartWool socks meant for cross country skiing because they’re thin enough to fit into my regular boots but warm enough for winter activity. I’ve rocked cuffed rain boots for most of this winter (and through spring) because they keep my feet dry during the slushy days and protect my jeans from salt and grit. At the same time, I do wish I had a better pair of weatherproof tall boots like these sold at Shoo on State Street:




Third layer: Outer gear. This is where my winter bike fashion took a major hit. I tend to wear my Patagonia puff jacket everywhere I bike in the winter because it’s flexible enough to move in while still being warm. It definitely stands out next to the black wool coats everyone else is wearing, but I hang it up as soon as I arrive. If anyone has recommendations for attractive jackets that work for winter biking, though, let me know!! I’m eyeing sales racks for next season.

In addition to my jacket, I also wear a thin ski cap under my helmet and mittens.

Fourth layer: Backpack or messenger bag. I’m a huge fan of biking with a bag for carrying my things (of course) as well as for stashing my mittens, hat, etc. when I get to a meeting or an event. A waterproof messenger bag is a classic choice, but a good looking backpack is a comfortable, spacious option.

I’m still working with the backpack I used in college, but I’d love either of the following options, both made in Wisconsin!

This black backpack from the Maggie Modena line is classy:

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A Beatnik Rolltop bag from Vessel Workshop in Milwaukee for a more casual vibe:

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My winter biking wardrobe is still a work in progress, but I’m looking forward to adding more pieces over the years.

I know what I want for work and ordinary days, but I’m looking for more ideas for nights out when I want something more fun than nice jeans and a sweater while staying warm. What have you found that works for you? Are their local designers making any bike-friendly winter wear that I should add to the list?


Rachel Keranen

Rachel Keranen

Rachel is a Madison-based writer who spent her childhood doodling clothing designs heavy on bell bottoms like a true child of the 90s. She's fascinated by how style impacts individuals and society, and she loves interviewing fashion entrepreneurs about their work.
Rachel Keranen

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