My badassness level at the office has definitely increased. I do have to admit a certain pride when I walk to my desk, helmet in hand, or better, leaving the office for the day, helmet in hand, while it's raining sideways outside. Although people may give me compliments on being tough and hardcore, in truth it's because I live by inertia, dislike change, and now can't give up my autonomy over transportation.
With the right gear, biking in the rain isn't much worse than waiting outside for the T in the rain. It actually may be better, because even if it's freezing, once you start moving your legs and pumping the pedals, you warm up. The body is its own little portable generator. The main problem I'm trying to solve now isn't staying warm; it's minimizing my sweating while riding.
So far I've landed on a few tips for biking in 25-40 degree weather. One is that I don't wear scarves anymore. they're a great way to keep warm, but having lukewarm sweat pile up on the back of your neck under said scarf is quite uncomfortable. If I can zip up my jacket to my chin when starting out, I can zip down a bit when I get warmer. The main areas of my body that are most subject to cold are my hands and my chin/neck. I did a bit of research and went and bought lobster type mittens-- gloves with a thumb and then two fingers. Two fingers fit into each glove finger, and can keep each other warm, and you are still able to maneuver the gears and brakes well enough.
Tomorrow I am going out to look at a mountain bike with disc brakes from craigslist. My current bike is a racing bike, a 2000 Greg Lemond that is the fastest bike I've ridden, and I love it. But it won't hold up in wintry weather, and I'd rather subject a less expensive bike to the icy sludge that will undoubtedly collect all over the wheels and gears. Also the disc brakes I've heard are very helpful when riding in dirt or snowy terrain, as they aren't dependent on the friction of brake pads against wheels like traditional brakes.
With luck I will be riding every day for the winter and beyond!