Head Cases

The year was 1837. A young entrepreneur, Klaus Z. Coconut, invents something called the "head shirt." Literally just a pulled-up T-shirt worn the over head like an inside-out head-sock, the head shirt revealed itself to be a horrendously stupid and more-or-less insane product idea within seconds, it's only real success being to convince the American people that, once again, they had confused the meanings of "entrepreneur" and "escaped, surprisingly industrious sanitarium patient." (A mistake that, sadly, they continue to make to this very day.)

But, though unquestionably crazy and likely possessing imbalances in at least two of his four humors (we're guessing phlegm and probably one of the biles), Mr. Coconut was onto something: Wearing things on your head is indeed awesome. The only catch is they can't look cheap, terrible or generally convince people that you're an escaped 19th-century mental patient who has either been over- or -underdosed with sweet, sweet laudanum.

Sure, it sounds absurd, but give it some honest thought: How often have you been walking through a hillbilly- or hipster-centric neighborhood and thought to yourself, "That is absolutely the worst hat I have ever seen, and, at the minimum, I would like to spray that person with a full-blast fire hose and scold them about their explicitly bad life decisions?" More times than you can count on two hands worth of fingers, right?

So here's the deal: Picking out good promotional headwear takes a bit more thought than taping a sequined beet to your head and strutting down to your local hipster post-ironic poetry frump. There is logic involved. Money, design sense and general, business-building rules of thumb. Frankly, it's a fairly complicated field, but if you're really, truly worried about coming off as some sanitarium-bound beet enthusiast, here are five quick tips to help keep your headwear promotions fashionable, profitable and cutting-edge.