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

Updated: Feb 8, 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
Headband with a pony tail hole by Pearl Izumi


Sunglasses help with more than blocking the sun from searing your eyes, it also deflect the cold wind from blasting into them. Trust me, if you find yourself hours outside on a weekly basis, good quality sunglasses will save your eyes.

Fluora Teal Frame by Roka
ROKA Performance Sunglasses

Try to find some with polarized properties (limits glare and reduce eye strain on sunny days) or cycling specific glasses with frames that wrap around your eyes. Roka has some stylish cycling frames. Oakley is also a very popular brand in cycling. I’d suggest buying sunglasses that you can try on so they fit you comfortably.


Gaiters can serve multiple purposes aside from being worn around the neck. It can also be used as a mask to protect from flying particles from hitting your face and absorb sweat. Here are ways to use a gaiter.


Your torso contains many of your vital organs and keeping them warm will help your cycling performance. This is where layers come into place.

  • Merino Wool Base layer - Merino (a type of sheep) wool is a fiber that helps keep your body at a stable temperature. When it’s cold outside, the material traps air and insulates you. When it’s warm outside, it wicks sweat quickly away from the skin, keeping you cool and dry. This is worn underneath your jersey as a long or short sleeve. Fabric technology has come a long way to produce a thin material that keeps you warm! Also a versatile piece to wear year round on rides.

  • Long sleeve (L/S) jersey - Kill 2 birds with one stone with this one. A long sleeve is a minimal way of riding. When researching bike specific clothing, check the season and temperature in which the jersey is designed for. “Thermal” is a common term found in winter clothing. If you know you run cold, you may need an additional layer on top of a L/S jersey.

  • Windbreaker/Jacket - If you have the above and are still feel like it's not enough, a wind breaker like material will help block out a lot of the breeze that tends to penetrate the jersey. Find one that is compact and foldable so you can stow it away once you’re all warmed up or whip it out again when you’re descending. This jacket by Gore is insulating, has removable sleeves, and back pockets.

  • Arm/Sun sleeves - Dedicated sleeves are a great way to add warmth and/or sun protection. It can be worn with short sleeves and also serve as a sun sleeve depending on the material. I personally own a pair of “sun sleeves” (adds coverage, breathable, and removable) that double as winter sleeves for me when layered with a wind-breaker.


Warm, mobile fingers make a world of a difference. Your hands do so much work from braking, shifting, grabbing things out of your pocket, drinking water, etc. If your hands get cold, it’ll be painful to bend your fingers when you shift and brake.

  • Cycling gloves in particular have padding in the palm area which helps give that added cushion as you rest your hands on the handlebars.

  • Cup of warm liquid - Take a pit stop at a cafe, grab a warm drink, enjoy the view. This is an opportune time to catch up with friends and your tummy will appreciate it too.


When you’re equipped with the proper clothing for the weather, riding becomes more enjoyable. Layers are important on rides with variable temperatures (whether it’s your body heating up or the weather warms up later). Knowing what your temperature tolerance is, you’ll be able to select clothing that makes the most sense to you for that day. My final tip is, wear just enough that when you start your ride, you're slightly cold. This leaves wiggle room to warm up because a comfortable cyclist makes for a happy cyclist.

Stay tuned for Part 2 where we cover the lower body (pun intended).