If you are considering doing #bikeTO through the winter, whether for commuting or recreational purposes, here are my tips + gear recommendations to keep yourself safe + warm, as a year-round commuter who often wears a dress (feel free to add your own suggestions):
Also, much of this is already covered in @CycleToronto's Winter Riding Tips page, which is great! They are great! Become a member, and if you do get your bike lock frozen, they will de-ice it for you!

https://www.cycleto.ca/winter-riding-tips
Tires: Studded tires aren't great for Toronto winters, but winter tires (like the ones for cars!) exist and they are amazing. Great for cutting through unplowed streets, for the snow that cars drag into bike lanes, and random patches of ice.

https://curbsidecycle.com/products/continental-top-contact-winter-ii-premium-tire
Hands: I previously dealt w/ cold hands by layering gloves, which limits dexterity + has diminishing returns.

Pogies/bar mitts keep my hands SIGNIFICANTLY warmer and have the benefit of protecting my brake cables from moisture, so my bike doesn't freeze.

https://curbsidecycle.com/products/45-nrth-draugenklaw-pogies-for-flat-bar?_pos=1&_sid=9a463e6ce&_ss=r
Ears: You can wear a hat/earmuffs, or you can get a helmet made for winter that covers your ears. I use a skiing helmet (but have been advised that they're not rated for cycling; apparently Bern makes a line of winter helmets: https://www.bernhelmets.com/collections/snow)
Neck: I am partial to a giant blanket scarf (on top of the gaiter), because I wear a moto jacket which leaves lots of neck space that needs to be protected from the wind, but if you're wearing a normal jacket with a high collar you're probably fine with any old scarf.
Body: Layers + materials that dry quickly/prevent you from getting wet.

I wear a (faux) leather jacket all year, but a colourful waterproof shell is probably safer! I've ridden in a dress & tights in -5C and been fine. Nothing worse than sitting in wet pants all day at work.
Also, I very much want to try Uniqlo's HeatTech line because I have heard great things!

https://www.uniqlo.com/us/en/women/heattech
Lights/Reflectors: Drivers mostly don't want to hit you, but it's much harder to avoid when they can't *see* you. And winter is full of darkness, inclement weather that reduces visibility, and slippery conditions!

Bright + shiny things = great.
I am very forgetful, so I got a mounted light. However, I also leave my bike outdoors, so all those lights eventually rusted and stopped working.

A dynamo light system fixed that problem beautifully (powered by your wheels! a closed system!), but it's not cheap.
Fenders: Good fenders are key to preventing a huge line of slush up your back and things in your basket from getting soaked!
Lock: To prevent your lock from getting moisture and then freezing, keep it lubricated and lock it so the keyhole points down. You can also probably carry a plastic bag to wrap it, but I am never that diligent.
Saddle: I love a saddle cover, because nobody wants to sit their ass down on a cold, wet saddle and then have a wet butt for the rest of the day. A plastic bag will do in a pinch.
There are lots of things to consider at first, but once you have all your gear and routines in place, winter biking can be so great! Much better than waiting in the cold for a late bus or streetcar and then getting on it and smelling everyone's wet clothes.
You can follow @ashley_quan.
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