"The Medieval eye found any surface in which a background could not be distinguished from the foreground disturbing. Thus striped clothing was relegated to those on the margins or outside the social order - jugglers and prostitutes for example - and in medieval paintings the devil himself is often seen wearing stripes."
The Devil's Cloth by Michel Pastoreau
This book is a fascinating ponder. I bought it years ago and through some research I am doing right now I have rediscovered it.
Instinctively I would think to use stripes in certain places for certain types of character - striped workwear for house staff, stockings for a saloon girl or an offbeat character, prisoners etc, then I'd worry my first thought was a cliche or stereotype. I had only a faint idea of just how far back in history these notions went and of how accurate a reflection they are of their historical origins. Michel Pastoreau's study shows just how fully absorbed into our psyche are these early notions of order and disorder.