Part 1: How to dress warmly in the San Francisco/Bay Area winter (starting from the top)

Updated: Feb 7, 2021

What I love about the Bay Area is that you can ride all year round. With the right gear as you transition into the seasons, it is possible to ride comfortably and maintain your fitness. Below are suggested items to mix and match if you’re looking to have a cozy ride on a chilly day, especially in the mornings. We’ll start with our heads, then cover the torso. In Part 2, we’ll go down to our knees and toes, knees and toes.

Note: While most of these items are cycling specific, you can totally supplement them with clothes you may have already that provide the same function. Come from a running or hiking background? You may have a dry-fit shirt, light jacket, or thin gloves, lying around which can do the trick!


Heat escapes darn fast from your head and a great way to keep that scalp warm (and protect from bees zipping into your helmet with their stinger, yes, that happens) is to put on a cap. Another benefit is the added shade to help you see better on the road.

2 kinds of cycling caps

  • Two-fer Cap (made this name up myself) - Basically, a hat that provides full head AND ears coverage for those chilly days. Keep in mind the material - you want one that can wick away sweat and still keep you warm. Check out this one by Pearl Izumi

  • Regular cycling cap - This works wonderfully year round for wicking sweat and offering some shade over the eyes. You’d be surprised how much less you squint with a cap!


Ears need some love too in the winter. Are your ears known for getting cold quickly where it can be painful?

Try a slim headband that can fit under your helmet for warmth and to prevent the sunblock sweat cocktail from streaming down into your eyes. This example below has a hole to pull a pony tail through. You can use this for other outdoor activities as well such as hiking and running.

Black handband with a pony tail hole