I would think about how you use your makeup. What drives you to pick item A over item B? Do you remember things by brand, color, type? It should be organized to make it easier for you to find what you’re looking for to use.
I would recommend finding products that wear exceptionally well on you and take longer to breakdown. I tend to like creamier products and find they are easier to pat back into place if things are really warm/humid. I also like a spray like Clarins Fix Makeup Spray to help lock things in.