I guess the closet that I've come is while at the First Friday concert in downtown St. Pete having someone talking their friend think that I was homeless. Until his friend started "dissecting" my bicycle, i.e. saying:

See those pedals (Crank Brother Eggbeaters)? He ain't homeless.
See those pannier bags? He ain't homeless.
See the bike he's riding? He ain't homeless.
See the kit that he's wearing? He ain't homeless.

The next was I was talking with one of the rent-a-cops at my complex and he told me that the first few times that he saw me that he thought I was coming to buy drugs. Like someone seeking drugs would have multiple lights on their bike, ride wearing a vest and a kit. . .