Sorry QuizTeamAguilera
Its become a well rehersed art form!
Obviously this is just what I take, if you are having a more chilled, relaxing beach type holiday with maybe the odd evening sat enjoying cocktails then you will probably not want a couple of my things, but would want a couple of other things!
Cycling shorts I take becuase they are so practical for me. I occassionally get sore thigs from too much sand / heat, so I like them as they give me a bit of protection.
The trainers and socks are not stylish but they are comfy and I do silly things like wondering round archelogical sites in the middle of the country side so they are both comfy and safe (for walking and for insects)
I have found that I can wear a saress with chucky jewlery, and either waterfall cardi or pashmina with healed sandles to a posh resturant, or with flipflops and big sunglasses to the beach (SO SO SO much easier for me than a sarong)
Boyfriend shorts and a vest with a cotton shirt over for wondering about town during the day, going down to the beach, catching a bus or driving in a hire car.
Maxi skirt, big wide belt, sandles / flip flops, vest top with or without shirt, cardi or pashima can do both the day in a posher town or the evening
What I have just done though is look up boyfriend shorts! The ones I have are so NOT like that, I have knee length chino style shorts they are very comfy but still smart enough to be able to wear out in the evening or during the day. Boyfriend shorts as they appear to be on nexk, gap etc, would NOT suit me
I think the trick with limited packing is to make sure that everthing you take can work together so that you can wear any combination dressed up / dressed down. Jewlery (cheap so you won´t worry about leaving it in the room) and Good sunglasses can really make a difference when dressing something up. Making sure that the colours and fabrics work is sensible to. ie I take about 4 or 5 colours in total but they all work with each other. Keep key peices plain and then add other colours with things like vest tops.
Have fun