Two things have completely change my perspective of riding in inclement weather:
- I got a really good rain jacket. It doubles as a great wind shell in cold weather! Probably 90% responsible for me heading out in less than ideal conditions.
- Fenders. Full coverage fenders make all the difference in the world. Butt dry. Feet dry. Drivetrain cleaner. Water bottles cleaner. Etc Etc.
It is really entirely possible to be comfortable in all conditions, just remember, there no such thing as bad weather. Only bad clothes.