Hahaha, this is too funny!. I am THE worlds WORST over packer. Put it this way, my suitcase, well I can fit in it and there's still room for the stuff I need.
What I took on my last trip:
Wedding dress and all the bits (tiara, veil, shoes, jewellery)
17 bikinis
14 sets of underwear
11 pairs of shoes (heels, wedges, flip flops, trainers)
19 vest tops (various colours)
9 pairs of shorts
3 short dresses
2 maxi dresses
10 mini skirts
1 jumper (it was cold when we left UK and returned)
1 pair of trousers
3 handbags
4 beach cover ups
1 inflatable pool lounger
7 kgs of toiletries, make up, sun lotion, plasters, bug spray, upset tummy tablets, nurofen, anti acid tablets, after sun, shampoo, shower gel, conditioner, deodorant, rehydration salts, paramol
3 plug adapters
Camcorder
iPad
iPhone
2 books and a few other bits and bobs excluding the kitchen sink.

What I should've taken:
4 bikinis
4 vest tops
2 dresses
2 shorts
2 flip flops (one a bit snazzier than the other so could be a bit sparkly at night)
Shower gel and two in one shampoo and conditioner
Sun cream and after sun
iPhone and camcorder and 1 adapter.
Wedding stuff

With the 'should've' list I'd of probably STILL had too much. I do it every single time. I take enough clothes to last me two months. I'm a 'just in case' person and it drives my hubby mad (he has to get the case in and out the car and up any stairs etc, or else he looks 'horrible' with me struggling with MY case and him with his little case that he could actually take as hand luggage).

Summary: you won't need anything apart from a few bikinis, passport, camera, money and a cover up or two and some mascara,clear lip gloss and a big bottle of your favourite conditioner from home (hair gets very dry), oh and a maxi dress.

I am going to look back at this post I've written in a couple of months when I pack to go away. Actually, I'm going away tomorrow (UK mini break) and I haven't packed yet LOL.

I miss Negril, been back home for a month and I can't wait to press the 'confirm' button when I book to return to Paradise!!!