usually have a helmet, but sometimes I want to feel the wind in my hair and I don't care for one when I go on short errands. I'll wear bike shorts under my pants when I know I'm going to be riding all day that day, I'm in a kit for the training rides, and both my bikes have clipless pedals. I wear plain old boxer briefs (they seem to work well against wedgies), jeans, T-shirts for my everyday riding