There's an encouraging article at The New York Times about bicycle tourism in Portland. The writer doesn't mention any special cycling equipment outside of raingear and he mitigates any trepidation about riding in the rain by mentioning how easy it is to do several times. Here are some more gems from the article:
There is a lot of energy around cycling right now and it’s not just 20-year-old men racing. I see average people out biking.
Roger Geller, Portland Bicycle Coordinator
It’s not unusual to see women riding through the winter in skirts and knee-high boots, followed by athletes training in winter riding clothing
Molly Shultz, Portland cyclist
Go ahead on, Portland with your smart growth and your cycling citizens! I wish all the other sprawling U.S. metro's had just a little bit of what you've got.