Useless Item #1

Lets begin at the begining. Under the category 'General Clothing' you will notice the first item recommended under 'other items to bring' is a Sun Hat. This is a particularly inauspicious start. It's not that Jamaicans don't wear hats, they do. In fact they wear a great variety of hats, unfortunately none of them would fall into the American definition of Sun Hat. If you wear around some funky straw beach hat you will end up looking like a perma-tourist and the taxi men will forever scream 'ochi' at you every time you turn around. In Jamaica, Older women wear hats to church, but this is a special hat that, if you never attend chruch, you won't require. They also wear hats that match their outfits; Blue slippers, white pants, blue top, white hat. That sort of thing. Young women generally don't wear hats at all, they opt for large hair clip-ons instead. Men who aren't rasta wear baseball caps, if anything, but they tend to prefer showing off their hairstyle.
Most Peace Corps volunteers do protect themselves from the sun, but this is accomplished with sunscreen. Your existence is enough to make people stare, a strange hat just moves you into the 'mad' category. In the end, it all boils down to the aforementioned Weird White People Behaviour.