Ok, apologies in advance , I am a bit of a packing geek and like to be organised. I start with a list of what i am going to be doing, and write down the changes of clothes i will need
Day 1
travel top1, trousers1, jacket, comfey but smart shoes, sunhat
Dinner in the evening top2, long skirt1, sandals
Day 2
Early swim swimsuit1 etc
Breakfast
After noon by pool
Evening dinner
Etc
This tells you how many tops, skirts etc you need. You may be able to double up on some, its always good to have one spare glamorous and one comfortable outfit for unexpected events
Now you pick which tops you take, you know how many you need. Check the sandals, bags etc all go, and that you have any special shoes, undies or jewellery required to finish the outfits.
Do all the planning on paper, where its easy to change your mind and juggle options. A day or so before you go, put out everything you plan to take, where you can see it all. Spare bed or a desk is ideal for this stage. Add / subtract as required leave it all out so you can see you have plenty. Add makeup, toothbrush etc and pack it all into the case, with the things you use last in first so they are at the bottom.
Enjoy stress free holiday packing. Keep the list of what you took for next time, and update it with good ideas. Enjoy.