Fundamentally, there is nothing wrong with a chequered shirt and jeans. It is comfortable, practical and is easy to look good in, but from a fashion point of view, quite uninspired. Nevertheless, there are far more interesting ways to wear chequers - whether it be a skirt, shirt or dress - which, I think, is at the cost of not much more effort. Just a well-placed scarf, jacket or belt can do wonders.
I personally like to wear chequered shirts as outerwear in the summer, rather than as a top. It makes the layering a little more interesting, and I love layering. And of course, there's nothing like stealing your mother's man shirt (so I call it) when she's not wearing it.
Click for LB