Going for the Laugh
Choosing the funny tie, the T-shirt with the great slogan or a pair of bizarre shoes works some of the time, but if the usual response to your clothing style is a chuckle, make more of your choices about your fashion sense than your sense of humor. There isn't anything wrong with dressing fun -- it just isn't always appropriate to the occasion, like work or formal functions, for example. Funny can be fun, but looking good and getting the laugh aren't always compatible goals.
It's also important to use an editing eye when piling on several different colors. While there's nothing wrong with mixing and matching colors, you don't want to look more like a clown than a fashion-forward man. Choose one or two bright pieces and pair it with a neutral: black, brown, navy, tan, beige or khaki. And don't think that wearing one color head-to-toe will fly, either. A purple jacket, purple tie, purple pants and purple shoes will only get you the nickname "Barney!" Imagine if you saw the same outfit on someone else.