Yes, if you know how to wear it the right way.
Yes, of course you can wear plaid.
With cirlces painted on your face and feet
You can if they are the same type of plaid but black or brown leather purse would probably look better.
How to Fashionably Wear a Flannel Plaid Shirt
New York Fashion Week Trends What's Fab: The Wild West
Ready to Wear Trends of Fall 2011
Michael Kors Fall 2012 Ready-To-Wear at New York Fashion Week