I'm admittedly a most of the gear all the time guy. I always have a helmet, jacket, gloves, but am not 100% on the actual riding pants and boots. Any trips or longer rides, I always have those on as well.
It's all about acceptable risk for me. I don't ride with sandals and shorts ever, but I'm ok with riding down to the store in levi's and tennis shoes. I don't go riding the canyons in them though. I realize I could do better, but I'm ok with not being 100% perfect about it.