I subscribe to the color matching method, Choose items that can easily be mixed and matched. Heavy shoes on feet, DH wears his deck shoes so only flip flops go in carry on. Me my deck/athletic shoes, sandals & flip flops in the suitcase. We carry on a rain style jackets (Columbia) super light weight, they are the fold up ones. DH has one of the fancy back backpack that protect your lap top and iPad and go pro, plus there is a ton of room for other items, for me I use my Vera Bradley bag( grand tour or weekender), DH has less liquid items so I "share" his baggies.
I also lay out everything that we must have, and then any extras all on the bed. Then lay out the bags, and work from there. I started doing this a few years ago and could not believe how much more I/we could take. I have a list of what activities and plans for our trip then make sure we have what we need, as I go down the list I throw them in the suitcase, then I start actually packing...arranging and rearranging for maximum space. Then add in any extras.