I've gotten used to wearing cycling gear whenever I go out for a ride if I'm commuting, exercising, running errands or whatever. I was really stumped over the weekend when I went to ride to a friends house to feed her cat while the friend was out of town. The trip was about a mile, and it perplexed me for a minute while I realized I really didn't need to change clothes to make the trip. It reminded me of when we just hopped on our bikes and rode somewhere when we were kids without thinking of changing clothes, because we never had to change our clothes when we did something fun.
I think you're on to something interesting Chip, keep us informed on how things work out.