For someone who is really, really cold-natured and from the tropics, I've surprised myself these past few weeks. Mainly by doing far better than ever before at riding in some genuine cold weather.

One weekend, I rode on a day where it was in the 20's with 25mph winds. Amazingly enough, I had to actually stop and remove layers. Ended up riding in a s/s jersey, arm warmers, shorts, and leg warmers, that's it.

The big caveat? I think you can ride in cold weather without wearing a large amount of clothes, but you have to be working very, very hard, like doing a long, hard climb. However, you do have to come down the mountain though, so that calls for serious cold-weather gear (aka that cool velo bella jacket I got ). In the flats or with variable terrain, I find it harder, but not impossible, to generate enough warmth without lots of layers.

Riding in deep snow is a whole other question. Not one I'd court on the road, though maybe on the MTB and a nice trail.

You could always get a trainer and ride the day away. Yes it costs money, but it is equally good for avoiding cold, rain, sleet, and darkness