Anyway you look at it, the checkered pattern look always makes you think of mom’s kitchen or the country look.  It’s been “type cast”.  The fashion industry tries very had when it comes to checkered fashions but people wear them in limited quantites due to the stigma that they have with relation to old ladies.  We use the checkered table clothes and napkins around the holiday seasons so wearing a checkered dress is more less like a costume than anything else.  Hopefully the “checkered” look will take off and we will get past those mental blocks that we have with regard to certain patterns.