I completely overpacked my first trip 10 years ago & have made a game of not overpacking since.
Like Prism, I can get away with just a carry on and a beach bag for a 10-14 day trip. 1 pair of pants , T shirt, and fleece hoodie all layered that I wear on the plane.

I bring a large sarong or a thin beach towel that I can use to sit/lay on or for shade if needed.

All of my clothes & sandals are tried & true. I don't usually bring new things. To me, nothing worse than being uncomfortable from clothes/shoes when trying to chill!

I color coordinate things. If I'm bringing blue & brown flip flops, I only bring clothes that will go with. The cute outfit that I need that one special pair of shoes doesn't go on the trip....unless a very special occasion!
No bling, only a few pieces that I don't mind losing.

No make-up, other than waterproof mascara.

I pack once, then start removing items
My goal, to not bring more than I can carry!