When I travel overseas, I carry very limited, light weight, wrinkle free clothes that can be worn in the day time as well as in the evening. For footwear, I had carried one pair of heels that I wore in milongas (I bought so many there) and throughout I was wearing comfortable flat shoes- Naturalizers. We walked so much there. I generally, carry 3/4th of my suitcase empty so that I can fill it with my shopping. Below, I am wearing the same dress in multiple ways. I have even worn backside front. It is by Desigual.
Here I have teamed it up with a cotton shrug.
Worn back side front. See the difference above and below.
Worn without the jacket.
More ways to wear the same dress is with leggings or with a T shirt on top. So it looks like a skirt. During vacations, when you have packet limited clothes, be at your creative best to utilize same garment in multiple ways.