Four helmets, not counting a taped-shell model that I bought in '99. First new one was a Giro Xen -- bought it because it was by far the most comfy helmet in the shop. Then got a road bike, and decided to go with a road helmet -- so I got a Giro Pneumo. Fits nicely, better vented than the Xen. Then, my LBS was getting low on its stock of Bell Metros, so I got one with the accessory kit; with its rain cover installed, it's easily my favored bad-weather helmet. Then, this spring, a friend got me a great deal on an S-Works, which is the best-fitting, best-vented helmet I've used.
I could sell the two Giros and not really miss them, but even though none of my helmets have been damaged, I'd be encouraging a potential buyer to go against my own advice: "Never buy a used helmet."
Two pairs of cycling shoes right now -- Sidi Genius 5 road/poser shoes and Specialized Taho MTB shoes. I'm looking to get some SPD sandals, too, as I've finally found some regular sandals that I enjoy wearing in the summer.