I hate to disagree with Ralph Lauren about anything, but my idea of preppy does not include baggy cargo shorts that fall below the knee. Preppy shorts should be slimmer, shorter, and made of quality fabric (especially stuff like oxford cloth, seersucker, and madras).

When wearing shorts I always wear a belt and tuck in my shirt. (I stay in shape and there's no point in covering up with sloppy clothes.) I usually go with an oxford cloth button-down or polo shirt, avoiding T shirts unless I'm on the beach. For me, it's a toss up between boat shoes or penny loafers. I save my athletic shoes for the gym or running.

I am partial to Nantucket Reds, which look great with a blue candy-striped Oxford. Embroidered belts are perfect for shorts. I'm the kind of guy who sees a picture like this and buys the whole outfit!
Now let's see, how many more months until summer?