In one of his songs, Kanye West says, "How am I supposed to stand out when everybody gets dressed up?". Well here's how: where a jacket and tie with shorts.
This is one of my favorite looks. If you have the grapefruits to pull it off, do it! I've only seen one other person (other than myself) do it, and it looked awesome on him! (Wish I had my camera).
The trick is to not be shy about it. Wear a slim tailored blazer, shirt, tie, dress shoes, as usual...just trade the pants in for a pair of shorts (and leave the socks in the drawer, of course). You also need the right pair of shorts. This look doesn't work with cargo shorts or basketball shorts. The shorts should be similar to the khakis or trousers you would wear with the same outfit; slim through the leg, neutral colored, and pressed. They should hit about an inch above the knee.