Goodluck marsha, your outfit sounds so effortlessly chic as always, my go to work related "uniform" is vanessa Bruno cream silk shirt dress and Marni skirt, specially if its a sort of a group meeting thing,
linus, I wear mine with heels or marant wedge boots, I have a pair of old caged tan sandals, from Gucci that look good with them too. they are tricky with most shoes, as they need to be really sleek and somewhat pointy if you want to make them look contemporary ,otherwise you end up getting those dent like creases around the ankle area, my mum tells me that back in the 70s, they used to apply starch to stop that happening,
But I think MIH have really altered the cut of the original flares, mine look more like wide leg jeans, which is what made me buy them in the first place, the new one and I'm not talking about the skinny flare , are really pronounced.
shop that sounds really good, you dont need much, and don't get coloured shorts, a pair of denim shorts, is all that you need its the best cover up,and can be worn for casual lunch by the beach, I wore my APC one last summer when we went to pampelonne beach,and just wore a simple slub tank top to lunch later, it was literally what everyone was wearing,
I wouldn't get trousers or silk shirts for dinner though, you will be on an island in the Caribbean! Your clothes should be more laid back and effortless, like you've just came from the beach, and just picked a random dress 
, put on sandals and lipstick, and volia!