You don't have to have it all worked out before you go, but I like to ensure everything I'm packing can be worn with everything else. This will give you many combinations / options even if you're packing very light. If there is one red top that matches only one pair of pants, it shouldn't come with. Everyone must get along.

Two light skirts? I don't think so. Three black dresses? Choose one!
Ask yourself, "Is this item doing the same thing as this other item?" and then pack the superior version.

Limited choice stimulates creativity. It's fun to pack experimental pieces like skirts that can be worn as dresses, dresses that wear well over pants, silk scarves that can be worn as tops / bandanas / belts.

Lush, breathable, lightweight. You can fit 3 silk pieces to one cotton tee. The crinkles? My friend Leisa taught me to hang pieces near the shower to steam them and you can also lightly spritz silk with water and it will dry without creases.

100% travel necessity that I've taken overseas on my last 10 trips and worn constantly. They unlock so many tops and are extremely comfy.

Accessories may seem fiddly but they don't take up much room and they can add a new spin to a repeated look. The same dress can be refreshed with a new scarf / little belt / necklace. I often like to grab trinkets along the way to help with this aspect.

Last year for me it was a reversible silk wrap dress, black on one side, sage on the other. It was minimal but always made me feel put together and I could wear it to the beach or dinner.

This old chestnut. Pack and leave 30% behind. I struggle with this myself. But there are always at least 5 things in my suitcase I never wear, the trick is selecting the weaklings. The more you leave behind = the more space for new finds. Imagine the heartbreak of going to a Spanish flea market and not being able to get anything cause your suitcase is overfull already? Channel this.