Packing can take me on some very long tangents, so it's good to have a game plan!  The best starting point to make the whole ordeal hassle-free = shoes! My clothing can mostly be paired with navy or black, so I pick one of those and get started.  White, gray, or tan may be your preference, so pick one and get to work. After I nail down the shoes, I can more easily pick the jewelry, sunglasses, and handbags to bring. Make the rest of your wardrobe work with those, instead of starting with your clothes, and you won't be stuck needing a million different options of shoes and handbags.  I just tried this trick and it definitely made my Memorial Day packing so much easier!
Turkish Towel: Charleston Weeender | Sunglasses: Dandy Boutique | Shoes: keds             Hat: Forever 21 | Earrings: Lisi Lerch | Watch: Sophie and Freda (Rue La La)