Dressing for the Winter

Living in a cool and wet climate and being a cyclist don’t always mix.  After 6 years of spending nearly my entire winter training in the Pacific Northwest, I’ve finally found what works and what doesn’t when it comes to dressing for the weather.

In Seattle, from November to March we tend to run into three types of weather; cold and wet, cold and dry, and not so cold and wet.  Finding the balance between being comfortable and warm without overheating or freezing can be a challenging balancing act for even the most experienced Pacific Northwest cyclist.  This post will share the knowledge I’ve gained over the years regarding clothing choices and hopefully encourage more people to brave the elements this winter.

Cold and Wet

Although we’ve had some mild winters in recent history, it’s not uncommon for my rides to be in 40 degrees and rain.  After years of trial and error, I have really nailed down the clothing choices that work for me.

Cold & Wet

Cold & Wet

From head to toe, my cold and wet training gear is as follows:

Wool cycling cap with a small brim

These are great for keeping your head and ears warm and also protecting your eyes from the elements should you need to take off your cycling glasses.

Cycling glasses with rose or yellow lens

I like the rose and yellow lenses because they give your eyes UV protection while brightening up the road making it easier to pick out obstacles and hazards.

Neck Buff

I love neck buffs, they’re just one more barrier between you and the elements and can easily be pulled up over the nose and mouth in really cold conditions or when you get stuck on a grimy and gritty road.

Thin wool 1/4 zip long underwear

I remember learning in Outward Bound when I was a teenager that “wool warms and cotton cools.” Wool will continue to keep you warm even when it’s completely saturated.  I have never overheated as a result of wearing a wool baselayer but I have certainly frozen when I haven’t worn one.

Fleece long sleeve jersey

The fleece long sleeve jersey is a must-have for many conditions.  I recommend getting it as tight as possible to not allow cold air to sneak in.

Rain Jacket

I am lucky this year that I have the Castelli Wind jacket with the windshear technology to keep me extremely warm and dry.  Many companies also make great rain capes which allow access to your pockets.

Heavy Neoprene Gloves

Using neoprene gloves in the rain has been a revelation for me.  Keep in mind that they only keep you warm when they’re wet so taking them out on a cool dry day is not recommended.  If I’m going to be starting a ride in the rain, I will often fill them with warm tap water and dump it out before I start the ride to ensure my hands stay warm.

Bib Shorts

Make sure whatever shorts you’re wearing have a solid rubberized and tight gripper to ensure they won’t ride up over leg warmers.

Fleece leg warmers

I much prefer leg warmers over knee warmers, I’ve personally never overheated on a training ride because I didn’t have 6 inches of exposed calf.

Wool Socks

I pretty much always wear wool socks if it’s under 60 degrees.  Again, my feet have never overheated due to wearing wool rather than synthetic socks.  There are tons of companies who make thin and warm wool socks which won’t make your shoes too tight.

Neoprene shoe covers

Much like the neoprene gloves, these will keep your feet warm even when wet.

Cold and Dry

Cold and dry conditions are some of my favorite winter riding conditions.  However, even when the sun is shining it can still be very cold and it’s important to dress appropriately.

Cold & Dry

Cold & Dry

From head to toe my cold and dry gear is almost identical to my cold and wet gear with a couple of key changes.  I would wear this in dry weather under 40 degrees and would stay comfortable down into freezing temps.

Crewneck wool baselayer

I have found that when it’s cold and dry the neck buff plus the high collar of my Castelli wind jacket are enough of a barrier to the elements.  Having the crewneck wool baselayer is generally enough to keep me warm.

Winter gloves

I prefer to use the Castelli Estremo glove for these cold and dry days.  They keep my hands toasty warm without having to use chemical hand warmers.

Not so Cold and Wet

Riding in wet weather when it’s in the mid-50s and higher can be really tricky.  It can be easy to overheat but starting and stopping or getting stuck in the wind can still chill you to the bone.  My trick has always been to wear layers that I can easily adjust or shed if need be.

Not So Cold & Wet

Not So Cold & Wet

There are still a lot of similarities between this outfit and my cold and wet and cold and dry outfits but still with a few key changes.

Traditional cycling cap

When it’s not so cold that you need your ears covered a traditional cycling cap can keep the rain and wind out of your eyes without being too warm.

Thin sleeveless baselayer

I LOVE the Castelli sleeveless seamless baselayer for these conditions.  It gives me a small extra barrier but the contoured mesh design is super breathable and comfortable.

Short sleeve jersey

When the mercury starts creeping into the upper 50s to low 60s, a tight fleece jersey can be overkill.  I prefer a traditional full zip sleeveless jersey.

Fleece arm warmers

Arm warmers are so nice in these conditions because they can be pulled above the wrist for additional cooling or shed all together if conditions change or warm up.

Wind Vest

I like a thin wind vest to just add one extra layer of protection against the wet and wind without overheating me.  Also, since I still go out in my wind/rain jacket in these conditions, should I start to overheat, the wind vest gives me options of small layers to shed to be able to keep warm.

Thinned-out neoprene glove

Much like the thick neoprene glove that I wear when it’s cold and wet, a thin neoprene glove will keep your hands warm but allow for increased dexterity.

Other Tips and Tricks

There are a few other little tricks that I use to help stay comfortable during long hours in the saddle.

Extra gloves

When a ride starts out dry but could cool down or get rainy, throwing an extra pair of gloves in your pocket is always a good idea.

Toe warmers

You can find the little stick-on toe warmers at most outdoor stores.  When it’s cold or wet I like to stick a pair on the outside of my shoe over the vent in the toe and then put my shoe covers on over.  Doing this covers up that vent and keeps my feel from getting cramped by having to put a toe warmer inside the shoe.

I also use the toe warmers rather than the hand warmers in my gloves.  In this case I just leave the paper on the sticky backing of the toe warmers and slide them into the back of my gloves.  I find these stay warmer longer and are less bulky than the hand warmers which are more meant for skiing and other snow sports where you don’t need to hold a handlebar.

Waterproof wallet

This is actually a nice thing to use year round (pro tip, don’t ever pay for a gas station bottle of water with a sweaty bill, it’s gross).  I use the “Witz See It Safe” on all my rides.  It holds about 6-8 cards and a little cash and is smaller than your iPhone.

Shedding Layers

Don’t under-dress just because you’re worried about having to schlep around unused clothing.  If I run out of pocket real estate on a ride, I will just shove unused clothing up the back of my jersey.  I’d rather ride with a clothing hump on my back than be stuck 30 miles from home without enough clothing.

Rain-X and Anti-Fog on your glasses

I use both Rain-X and goggle Anti-Fog on my cycling glasses to ensure I can keep them on even in the pouring rain.


Use your front and rear lights when riding on roads shared with cars.  It’s just safer.  However, when riding on the trail, make sure to switch your lights from “blink” to “steady” to be respectful of other pedestrians and cyclists.

Thanks for taking the time to read my tips and tricks for winter riding.  I hope it encourages more people to brave the elements and enjoy the outdoors year round!

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