As summer nears its end, I'm very curious to know what everyone does to handle the rain. For myself, I throw on a pair of rain pants over rubber rain boots with a GoreTex rain jacket.
At my work desk I have an old pair of Toms shoes that I bought at Goodwill that are super comfortable - I slip into them when I arrive and out of them when I leave.
I have a waterproof Timbuk2 saddlebag-style pannier, which I use to bring my lunchbox.
If you're intimidated by riding in the rain, give it a try! It's really quite invigorating and people will think you're either crazy, or a badass. Both seem fine to me!
Full front and back fenders are a must for me. I also have a poncho made for biking and it's kept me dry in HEAVY rain. My poncho was expensive, think it was called "the people's poncho" but I love it. Even keeps my legs dry, and the hood can go over my helmet - but I don't love doing that cause I feel like I can't hear or see much and it doesn't feel as safe.
Just got our first snow this week so I just put my studded tires and pogies on!