How to Dress for Winter

Winter time equals trainer time, right? For many, especially those who live up North, that is indeed the case. The only way to get in g...


Winter time equals trainer time, right? For many, especially those who live up North, that is indeed the case. The only way to get in good riding time is set up the trainer and load up Zwift (or your favorite Sufferfest). But trainer time is BOOOORING, and down South, our winters tend to be milder, meaning we have greater opportunity to keep riding outside. It can be cold, no doubt, but it is frequently less wet and snowy and icy than up North, and as long as you have daylight (or a good set of bike lights), then layering appropriately will keep you comfortable for the long miles ahead.

Here, I've created a guide showing some of my favorite winter apparel and how I typically layer them for the coming winter months. I've broken the guide down into 10 degree temperature ranges, starting with sub-70 F degrees. (I found that writing it all down helps, since every winter I meticulously experiment to find that perfect mix of winter clothing, only to forget it all in the following summer months.) Feel free to comment with you own mix of winter gear below (and check out my Gear List 2015 for more detailed reviews).


60-70 Degrees F


Here, the temperatures are cool and comfortable, and riding in your normal summer jersey and warm weather gear actually feels good. But during the spring and fall, the mornings can sometimes start a bit on the cool side, or the day may throw a bit of rain your way. Here is where I break out my trusty gilet. It's enough to keep me warm if I need it to, and will help keep me dry in a bit of rain. But it's also tiny enough to easily be packed away into a jersey pocket if needed.

Cycling Kit: Castelli. Sticking with the summer gear, here.

Cycling GiletBontrager. Serviceable, and purchased on a discount. If it's a bit rainy, or juuust a touch chilly (and will maybe get warmer over the course of the ride), I'll throw on this gilet to ward off anything unexpected.

Summer Cycling Gloves: Bontrager. Again, any summer pair will do.

Summer Cycling Socks: Whatever summer pair you prefer.


50-60 Degrees F


This is where I really start to feel it. In this temperature range, it's not cool enough to really break out the full winter gear, and since it's typically fall or spring in this temperature range, the sun will eventually warm things up a bit anyway. So this is where I really like to layer. I stick with my usual summer kit, but throw on a short sleeve baselayer underneath my jersey, and add extra arm warmers and knee warmers that are easily removed and stowed later as needed. I switch out my gloves to a long-fingered fall pair, and throw on a thicker, wool pair of socks to wear with my normal road shoes.

Cycling Kit: Castelli. Sticking with the summer gear, here.

Short Sleeve Base Layer: Gore with Windstopper. This features windstopper material on the front, which makes it loud and crinkly, but is quite wonderful in cooler temps. It's short-sleeved, which makes it perfect for layering on those in-between days so you can throw on and off a pair of arm warmers as needed.

Cycling GiletBontrager. If it's rainy, or I need a touch bit more oomph, I'll throw this on, too.

Arm Warmers: Castelli. Notice a pattern, yet?

Knee Warmers: Castelli. Save the knees! Knees work better when they're warm. Anything below 60 for me and you better believe they are covered.

Fall Cycling Gloves: Gore. Or any fall, long-fingered gloves here.

Winter Cycling Socks: A cushy pair of merino wool will do, here.


40-50 Degrees F


I feel like I'm cheating here, Now that I have a good winter cycling jersey, a pair of bibtights, and winter road shoes, dressing for this temperature range is easy. Paired with my absolute favorite baselayer, a skullcap, and really thick gloves, I'm good to go to miles and miles and miles...

Winter Cycling Jersey: Castelli Gabba. Wind-resistant, water resistant, and warm.

Long Sleeve Base Layers: Craft Active Extreme. These are the best you can get. Insulating, breathable, long in the torso, and high in the neck.

Winter Cycling Bibs: Gore Power 2.0 Thermal BibTights with Chamois. Soft and warm on the inside, and featuring a friggin drop-bib, meaning that the back zips down for easy peasy nature breaks. Humans should have thought of this sooner.

Winter Cycling Shoes: Northwave Artic [sic] Commuter GTX Boots. The only solution I have ever found to end my struggle with cold feet. Don't cycle in pain! Try these! They are a revelation.

Winter Cycling Gloves: Pearl Izumi PRO Softshell. This is the men's version, but I got them at discount and they are warm. And really, that's all you need in winter.

Winter Cycling Socks: A cushy pair of merino wool will do, here.

Skullcap: Pearl Izumi. I got this one years ago and have been using it since. Mine doesn't look like the picture, but one seems pretty much like the next.


30-40 Degrees F


The only thing I add on in this temperature range is my extra special, superbly warm Giordana winter jacket. On really, really cold days I whip this puppy out and put it on over everything else and I'm ready to roll. Well, I maybe throw on a pair of knee high socks, too, but that's basically it!

Winter Cycling Jersey: Castelli Gabba. Wind-resistant, water resistant, and warm.

Winter Cycling Jacket: Giordana Silverline. When it's really cold outside, I pull on this cycling jacket over my winter jersey for an additional boost. It's intensely comfortable and extremely warm. I can wear this thing down into the 20s. If I choose to still ride outside then.

Long Sleeve Base Layers: Craft Active Extreme. These are the best you can get. Insulating, breathable, long in the torso, and high in the neck.

Winter Cycling Bibs: Gore Power 2.0 Thermal BibTights with Chamois. Soft and warm on the inside, and featuring a friggin drop-bib, meaning that the back zips down for easy peasy nature breaks. Humans should have thought of this sooner.

Winter Cycling Shoes: Northwave Artic [sic] Commuter GTX Boots. The only solution I have ever found to end my struggle with cold feet. Don't cycle in pain! Try these! They are a revelation.

Winter Cycling Gloves: Pearl Izumi PRO Softshell. This is the men's version, but I got them at discount and they are warm. And really, that's all you need in winter.

Winter Cycling Socks: A cushy pair of merino wool will do, here. Or knee highs. Gotta love a thick pair of knee highs.

Skullcap: Pearl Izumi. I got this one years ago and have been using it since. Mine doesn't look like the picture, but one seems pretty much like the next.


20-30 Degrees F

Fuck that shit. Throw on a Sufferfest, baby!

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