Essential Wardrobe Pieces for Your Winter Commute

Ok, when I talk about winter, I'm talking about temperatures that range from 30-65 degrees. In Virginia, we get some quirky weather, and with climate change, I expect quirky to be the norm. We often will have cold rain, but very little snow. If there is snow, I'm not riding in it because we Virginians can't even walk in slush, so I would love to hear from some of you from different climates about your essentials. Without further ado...

Ear-muff headband 

It may be because of my ample bone structure, but my resonance spaces of my forehead and nasal passages always freeze on early morning rides. To keep my sinuses from freezing, I wear an ear-muff headband beneath my helmet, which leaves enough room for my hair and keeps me toasty warm.

First ride on new cargo bike.


To avoid frozen fingers, grab a pair of gloves, even the cheap dollar pair from Target. My gloves of choice are stretchy, tight fitting, and have a gripping material through the fingers and palms for easy brake handling and phone checking.


Even though it’s cold, you’re going to sweat if you’re going any real distance. I like to wear a light undershirt to catch moisture before it hits my shirt. I also like to keep layers loose enough for air circulation. The wind might be cold, but it certainly feels fresh when you’re breaking a sweat trying to make it to that meeting on time.

Tall socks (not a fan of tights for long rides)

If you’re wearing a skirt or need to roll your trousers, you’re going to need something to cover the skin. Though I love tights, I don’t like riding in them due to the waistband roll-down and the crotch ride-up or slouch, depending. I’m a big fan of knee-high socks, or just any sock that can clear the necessary distance.

Boots/shoes with good tread 

I never change my shoes for a ride. I often do 10 miles rides in heels. I do this by choosing shoes with good tread. My favorites are made by Timberland and I have a new favorite pair from iRi NYC. The soles should be rubber and have a fair amount of texture. It also helps to have a shoe that is flexible, though I have a habit of riding in some pretty rigid wooden platforms.

Favorite riding shoes


You gotta cover your chest. And sometimes you have to cover your mouth and nose (especially during COVID). Things to keep in mind: 

  • You don’t want too much fabric so it doesn’t get stuck in your wheels or drivetrain. 
  • You want enough fabric to comfortably cover from your nose to your chest.
  • You want it to be easily adjustable for temperature changes, so choose a wider cut.
  • You want a quick dry fabric.

Waterproof coat/jacket/cape 

I’m a big fan of my vintage wool cape for milder winter days, but I can’t ride with a backpack. I often opt for a lighter jacket below a windbreaker unless it’s REALLY COLD and I reach for my down filled coat. Inevitably, I become overheated once I start moving or ride home in the afternoon, so that’s where the scarf and layers come into play.

Again, in Virginia and most of the more temperate/subtropical climates in the US there can be a huge variance in temperature from day to day and morning to evening. My winter gear list is based on the need for versatility. 


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