I have no advice for glasses, but as for getting wet, my advice is this:

skin dries fast.

My habit when riding in the philadelphia area last summer was to ride in shorts, and no shirt. If you want the best chance of being fairly dry when you get where you're going, wear as little clothing as possible. For me, briefs rather than boxers. Non-baggy, not-very-long shorts made of quick-drying synthetics. For my feet, i would put on aqua-socks, though I imagine sandals could also work well. I would put on a shirt and switch shorts when I got where I was going.

For the rest of my stuff, i figured a way to bungee-cord a plastic tub to my rear rack. perfectly waterproof when held upright.