There's something inspiring about seeing winter bicyclists bundled up and pedaling down the street, snow and slush be-damned. When the rest of us are frigidly waiting for the subway or rushing to the car to crank up the heat, these brave (or foolish) souls are sticking it out, year round.
I always wanted to be that hardcore. Funny thing is, it's actually not that hard. When winter came around, I didn't want to come down from my newly-acquired bike high and take the germy crowded T every day. The thought was saddening. So I decided to make it happen. I would bike in the winter. The realization that I could put the $80/month that a subway pass costs towards bike gear sealed the deal for me.
You can do it too! Here's a short list of the gear that has enabled me to go out no matter the weather. I also want to point out that you don't have to break the bank to do this.
Bike suitable for winter. While I love my Lemond racing bike tremendously, I knew that those sleek thin tires just wouldn't cut it in the snow and ice. I scoured Craigslist and found the perfect bike. The K2 Zed. It has front suspension, and thick tires (not quite as thick as the fatbikes, but that would be overkill for me). Although it is heavy, that equates to stability in windy conditions, which has been a nice perk.
Waterproof, yet breathable outer layer. You'll have to choose what works for you based on your commute. But for winter sports in general, layering is key. I got a nice, used snowboarding jacket off eBay with zippered vents that are key.
Layer your legs. When the temperatures drop, if you're clad only in jeans, your thighs will freeze. I'll do either a long underwear under the jeans to add warmth or add rain pants on top of the jeans to cut the wind does the job.
Protect your extremities. Head, hands, feet. Making sure these areas are adequately covered can mean the difference between a great ride and a miserable one. For my head, I wear a beanie under my helmet, and a scarf wrapped around my neck and lower face and buckled under my helmet strap. For my hands I have a few pairs of gloves for progressively colder weather; and for feet I'll do wool socks, and hiking boots for the coldest or wettest days.
Honestly, winter biking hasn't been that hard. In some ways it's better than summer biking because you don't get to the office drenched in sweat.
I would recommend winter biking for those who are already familiar with their city's streets and traffic. If you're just starting urban biking, beginning in the spring or summer will be much easier. The learning curve will only be compounded by bad weather and erratic road conditions. But it is totally doable.