Hi!
I generally agree with the posts here, and especially agree with frankk : wear what you are comfortable in.
While Negril is the capital of casual, you will notice that some people choose to dress for evenings. Sometimes it feels good to take a nice shower and dress in a smart outfit after being on the beach all day.
As a woman in my mid-30's who is on vacation to see the sights, enjoy the beach, and visit with friends, going out for dinner and dancing in shorts and a tank top is perfectly comfortable. I've even been out at Bourbon Beach in a bathing suit and cover up dress. Everything I wear is clean and clean cut (no ripped or cut off clothes at night (or in the day for that matter, but that's just me and my wardrobe)). I have worn lightweight pants before in the evening and felt comfortable, but in general, with shorts, dresses, and skirts, nothing goes beyond the knee. I don't wear a lot of jewelry anyway, so I don't bring anything more than that for vacation. I've only vacationed with a man at an all inclusive a few years ago (I'm solo for now), so he adhered to the dress codes of the restaurants we ate at- dress shorts (his were Izod brand), and dress slacks (Izod, too). The wonderful man-friends I have vacationed with in Negril generally wear shorts and shirts in the evening.
I would consider where you are planning to eat - some restaurants have a dress code. I look at the general pricing and decide what is appropriate to wear. If you don't have that kind of a plan, or like to play it by ear, what do you imagine for your evening meals - wander the beach and get a bite to eat, jerk chicken barrel along the beach road, or make a reservation for a special night out? I could dress differently for each of these situations. All inclusive hotel restaurants have posted requirements, of course.
I would also consider what you want to do in the evening. Hanging out on your porch? you might want long, linen pants to ward off potential biting buggies. Going to the night club, you might want to dress to impress. Typical music venue on the beach, I'd focus on personal comfort.
I am trying really hard not to over pack this coming trip. I always focus on the what if's, but I've decided to make a plan and stick to it. I know what I want to do while in town and I know which clothes I will be comfortable in for each of those activities. I'm bringing swim wear, shorts, a skirt, a knee length dress, and tank tops. That will take me from wake-up to bed-time on the beach and in town.
Packing is my favorite pre-trip activity. I can't wait to throw open the suitcase and get it done in April!
