How to Dress for Biking in the Winter and Still Look Stylish

When it comes to bicycling in extreme weather conditions, I’ll skip the ride. Pouring rain, extreme cold, heavy snow, and slippery ice all put me on the subway, the bus, or in an occasional taxi. But when the temperature is above 25 degrees Fahrenheit (-3 Celsius) and reasonably dry, I will take to the streets on my trusty cruiser and some considerable, cold-crushing armor.

In my experience, the worst part about riding in winter is cold air reaching my skin. I can handle cold air on my face (to a degree), but I find it extremely unpleasant when freezing air blows onto my ears, down my chest, onto my hands and wrists, or onto my ankles. In harsh winter temperatures, I dress to avoid exposed skin as much as possible.

The necessities for optimum skin coverage are a good wool or cashmere scarf long enough to wrap around my neck, leather gloves, and a hat. I prefer a nice faux fur-lined trapper hat. From there, my core insulation drill is more nuanced between 25 and 50 degrees (-4 and +10 Celsius). Cool, but not quite cold, I’ll reach for my vintage pea coat. For cold, it’s a wool topcoat, scarf, and gloves at least. A tie helps, too, when I’m in a suit. At or below freezing, it’s a scarf, gloves, and hat with possibly a puffer jacket. And, for an extra touch at all temperatures, smart eyewear (sun or optical) to divert the cold wind from my eyes.

When bundling up for commutes to places with heat, long underwear or any base layers are out of the question. The physical movement of the ride itself is enough to warm me, even once I’m indoors. Thick sweaters and thermal underwear when I’m inside makes me not just overheated but also cranky. Once indoors, I want to be in my regular, normal weight clothes so that I can carry on comfortably. For those rides, outer layers rule. When I’m in a wool suit or in jeans, I’ll wear an insulating vest over my indoor clothes and under my outer jacket or coat. And good jeans made with 12-ounce denim (or heavier) are a good option. Thinner suit trousers stay neatly stowed in my bag for a quick change in the men’s room when needed. If it’s extra cold, I’ll throw a wool cardigan into the mix. I try to keep my ankles warm with wool socks and sometimes chukka boots.

If I’m out for a leisurely ride for an hour or longer in the winter cold, then I’ll consider long johns, but that depends on how cold it is and how long I plan on being outdoors.

With good coverage for those winter bike rides, my only exposed skin is my face, and it can take a beating when riding against a cold wind. For protection, good moisture is in order. A rich face cream keeps the skin protected from windburn. And I can’t live without a good lip balm, which protects the lips and keeps them moist and soft. This is, perhaps, most important if there’s a kiss waiting at the other end of my ride.

George Hahn is the creator, writer, and crash test dummy of his own website, a journal for men who aren’t millionaires but who like to look good and live well. georgehahn.com