@TheOriginalClownfish I do something similar with my regular and holiday wardrobes, have a signature colour and then add complementary and neutrals to mix and match
But consider how cut/style goes together too, I usually tend to the floaty/loose for tops and more fitted for bottoms
I've actually not been on holiday for years but I'm an expert packer! (Military brat!)
My tips are:
Wear your heavy items on the plane - coat, jeans/joggers, trainers so they're not tipping your allowance over and taking up too much room.
Underwear - no of nights you're away for + 3 in cabin baggage if taking hold and cabin
Yes to fancy flip flops! Super flexible option.
My thing I love to take is spaghetti strap camisole tops (£1.80 in primark!) I have tons! They are also super flexible! can wear as they are, work as a cool pj top, over swimwear, under sarong tops/dresses so you're not worrying about a potential "wardrobe malfunction and I've even used them on occasion as a "shrug" on dd when she was little and felt a chill and she'd refused to bring a cardi! 
Which brings me to sarongs/floaty scarves - extremely versatile and handy as clothing, blanket, makeshift bag etc
Comfort is most important thing but I've long since stopped worrying about other people being offended by me in a cami top just cos I'm short fat and nearly 50! When it's 30°!! Fuck that shit!